


Sunday, Bloody Sunday

by DeanstielsDaughter



Series: In My Hands [2]
Category: Supernatural
Genre: Demons, Destiel - Freeform, Fighting, Gen, Hell, M/M, Mythology - Freeform, OC, Original Characters - Freeform, Realms of Hell, Sabriel - Freeform, Team Free Will, season nine
Language: English
Status: Completed
Published: 2015-09-07
Updated: 2015-09-07
Packaged: 2018-04-19 12:37:14
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 11
Words: 23,541
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4746713
Author URL: https://archiveofourown.org/users/DeanstielsDaughter/pseuds/DeanstielsDaughter
Summary: <blockquote class="userstuff">
              <p>Dean received a distress call from Crowley stating Abbadon disappeared into Hell without a trace and is now waiting for the Winchester's next move. Now Team Free Will must once again leave the human world behind, descend into Hell, and battle the other side. Will they be granted victory or will evil reign supreme?</p>
            </blockquote>





	1. All Hell Breaks Loose

Team Free Will was once again on the road. Without a word to Sam or Gabriel Dean had driven off with Castiel riding shotgun and Kevin Tran and Titan in the back seat of the Impala towards Minneapolis. They'd been driving non-stop since two days prior when Crowley had sent out his distress call to Dean. Dean hadn't trusted Crowley since the whole trials ordeal, but while he and the unofficial rest of Team Free Will had been restoring Heaven to its former glory, Crowley had been amazingly assisting Kevin in locating Abbadon their other threat. He'd left the bunker after having tracked her for months and now once he'd finally gotten the drop on her in Minneapolis he'd been injured when Abbadon attacked him. He'd called Dean late one night informing him that Abbadon had disappeared somewhere in Hell's underbelly and that he now needed Dean's help in finding her.

Dean and the rest of Team Free Will had spent a few months without realization making their way through the seven Realms of Heaven, fighting various threats such as seemingly vicious Angelhounds, the flames of the Soul Train and even Metatron himself. Chuck Shurley, a supposed Prophet from earth that Dean, Sam, and Castiel had met long ago and who had disappeared from the face of the earth had showed up to help defeat Metatron once He realized the Winchesters were in Heaven and in trouble. As it turned out Chuck had been God in disguise all along and had cast Metatron down to wherever, dethroning him, leaving Team Free Will unharmed, and a once graceless Castiel redeemed and up to full power once again. All had ended well and Team Free Will had returned to earth unscathed and a hell of a lot happier than before. Gabriel had dragged Dean's brother off on a romantic excursion to somewhere the others had no idea about, but Dean knew as long as he was with Gabriel, Sam was safe. Castiel and Dean had been working on their new found relationship as well since the both of them had finally admitted a long hidden truth to one another; they loved each other more than friends and had for a long while.

Currently Dean was driving way too fast towards Minnesota with Castiel in the passenger seat staring out the window, Kevin in the backseat, and Titan, the Angelhound which had bitten Dean's ankle and that Balthazar had decided to give to Dean, leaning his head out the open window and drooling down the highway. Kevin seemed a bit uneasy with the hound right next to him.

"Oh c'mon Kev," Dean laughed, looking back in the mirror at the Prophet who currently had a lap full of Angelhound butt. "He's a real sweetheart."

"Dean," Kevin grimaced. "I have a dead dog on my lap, a living, breathing, dead dog."

"Ain't that the most ironic sight you've ever seen," Dean chuckled and looked over at his boyfriend who was watching the trees fly by. Castiel had offered to fly them all there, but Dean had decided they were driving, no questions asked. "Right Cas?"

"Oh yes," Castiel said, he seemed a bit distracted. "Absolutely Dean."

Dean sighed. Castiel had been acting a lot different ever since Heaven had been restored. Dean had been meaning to sit down with the angel and talk to him about it all, but once he received that phone call from Crowley everything 'normal' about their lives had gone to Hell once again.

"I sent out a prayer to Gabriel," Dean said, changing the subject off of Castiel. "He said he and Sam would get there before us, but they needed a day to get their bearings together."

"What about Balthazar and Lucifer?" Kevin asked, still trying to somehow push Titan off of him, but failing. "Have you spoken to them?"

Since Heaven's restoration, Lucifer and Balthazar were now both back in Heaven seeing that things were tended to. Lucifer had redeemed by Chuck after he'd decided to help the Winchesters and his home. He'd resigned from his original position as head of the Distinguished Angel Council and had let Donathan keep the position. He'd become a Warrior again instead and had been working with Balthazar and the other angels to restore Heaven to its once former glory. Dean hadn't heard anything from any of the angels but Gabriel and Castiel. All in all it had been fairly quiet in Heaven.

"They've been busy," Dean explained. "I didn't want to bother them, but I suppose if we're going to deal with the Queen Of Hell, we'll need all the help we can get."

At the mention of her name Titan growled and stood at attention, leaving Kevin completely smothered in dog. Dean and Castiel laughed.

"That's right buddy," Dean took his hand off the wheel for a second to pet behind Titan's ear. "We're gonna kick her ass."

Titan barked and lay back down on Kevin's lap earning a sigh from the Prophet causing laughter to once again erupt from the front of the vehicle.

-8-8-8-8-8-8-

It was around dinner time when the trio and Titan reached the heart of Minneapolis. They checked into some dirty run down motel. Titan housed the power to turned invisible if need be so with a quick order by Dean he did. The hotel manager checked them in and they carried their bags up to the room and shut the door. Once they did Titan turned re-visible and barked once, hopping on one of the beds before lying down on it.

"Ssh," Dean scolded him and Titan's ears drooped with a whine. "Do you want people to kick us out? Keep it down will ya big guy?"

Titan rolled over exposing his belly and whined for Dean to rub it. Dean rolled his eyes then sat down next to the Angelhound and proceeded to scratch his tummy earning a string of happy noises to come out of his muzzle. Kevin smirked, but didn't comment. Castiel simply sat down on the couch in the room and waited for Dean say something.

"Crowley called me on his cell phone," Dean explained their current situation to the room while Kevin and he unpacked their belongings. "But since he is practically human I assume he'll have traveled to one of the hospitals in the area to heal. I'll need Sammy and his hacker skills for that."

"Look no further Dean-o," Gabriel and Sam were suddenly standing in the center of the room. Sam looked very jet-lagged and Gabriel was smirking. "For we have arrived."

"Gabe," Sam held his stomach for a moment. "Did you have to do that so fast?"

"Sorry Samsquatch," Gabriel leaned up and kissed his cheek. "Dean-o here said he needed our help quickly."

Dean took in the sight before him. Long ago Dean hated the trickster, later known to them as Gabriel, and wanted to kill him. Sam did too. But something had happened up in Heaven and the two had decided to profess their mutual attraction as well. Dean wasn't bothered by it so much anymore, he'd originally been jealous; he just wanted to see Sam happy.

"Damn straight," Dean tossed Sam his laptop which Sam caught and immediately gave a bitch face to his brother. "Sammy I need you to check the records of the hospitals of any males admitted into any hospitals nearby."

"Dean that could take hours," Sam complained. "And that could be anyone! It could take forever to find Crowley among them and besides he'd probably never use his real name!"

"Figure it out Sammy!" Dean said, grabbing a beer from the mini fridge and popping the lid. "It shouldn't be that hard, just look for anything unusual."

"Oh and what are you going to do just sit on your ass with Cas and that hound of yours?" Sam sat down at the table, opened up his computer and started to work.

"That's the plan." Dean smirked and petted Titan's head before motioning for Castiel to join him on the bed.

"Lazy ass jerk." Sam grumbled.

"Bitch," Dean replied, missing the little things like that with Sam. "That archangel of yours not giving you enough? Or is it that stick up your ass?"

Sam rolled his eyes and started to work earning a hearty laugh from Dean as the older of the Winchesters cuddled up to his angel and affectionately kissed Castiel's forehead. Dean wasn't much for public displays of affection, but with Castiel and in front of his family he was okay with it. They already all knew, so why not? He looked down at Castiel who was zoned out and watching the television Dean had turned on, laying his head on Dean's chest and snuggling into him. Dean smiled and clicked the volume up a bit just as Looney Tunes came on. Castiel smiled and sighed contently into his hunter's chest.

-8-8-8-8-8-8-

"So get this," Sam spoke up a half hour later and earned everyone's attention. "There have been only two people admitted in the past two days that seem similar to Crowley. One is a Mr. Crowson; a similar name to Crowley's but the appearance doesn't match. The other, a Mr. Fergus Singer, perfect match it seems. Possible injuries sustained by Abbadon match too."

"Fergus is the name of his vessel," Gabriel spoke up. "And Singer, Bobby's last name perhaps it was the only one he could think of?"

"I have lost people too, people I cared about."

The voice of Crowley echoed in Dean's mind as Gabriel said that. Crowley had in fact, with an exception of Meg, been the most human of all the demons Dean and Sam had ever encountered in their lifetime. If he had in fact lost people he actually could care about, had Bobby really been one of them?

"Well," Dean said, getting up from the bed and shedding Castiel and Titan from on top of him. "That's the best we've got so I say we head on over."

-8-8-8-8-8-8-

Dean parked the Impala as far away from the hospital's security cameras as he could. Sam, Kevin, and Titan exited from the back and front seats and Castiel and Gabriel landed a few feet away at the hospital's entrance. Gabriel motioned for the rest of them to follow.

"Titan," Dean ordered. "You may wanna go invisidog on us; you can come in just stay hidden okay?"

"You got it boss," Titan spoke through Dean's mind to him and turned invisible before they entered the hospital's front doors. "But are you sure this is a good idea? I mean we just fixed Heaven. What if we're in over our heads here?"

"Not like I haven't faced the impossible before." Dean muttered to his invisible hound and shut his mouth when they reached the front desk. "We're here to see Mr. Fergus Singer?"

"Ah yes," the nurse said. "He was talking about you all nonstop, wanting to see his family. He's right this way and lucky to be alive. He sustained possible life threatening injuries is he hadn't gotten here sooner."

Dean and company followed the nurse to Crowley's room. Dean was shocked Crowley had referred to all of them as his family. He resisted the urge to pet behind Titan's ear for fear of looking crazy, but in all honesty it soothed him sometimes to have the hound nearby. They all strolled into Crowley's room and were greeted by the ex-demon's smile. He was hooked up to an IV in a hospital bed with a not so great view of the outside parking lot. He had a few scars on his face, but he looked as if he was on the mend since the two days prior when he'd first called Dean.

"You're looking well Dean," Crowley remarked. "As are you Sam. Your angels treating you well? Hey Kev."

"You look better than I'd anticipated." Dean said, sitting down in the chair next to Crowley's bed. Titan whined and placed his head on Dean's lap. Dean looked around for cameras and gently started to stroke the fur on the invisible dog's head.

"And I see you brought that hound of yours with you," Crowley chuckled. "And how you got him by security."

"Cut to the chase Crowley," Gabriel said, looking up to the clouds outside the window. "Where did you last see Abbadon before she got the jump on you?"

"Patience grasshopper," Crowley replied. "I was in an alleyway a few blocks from here when I spotted her; she put up a hell of fight. I zigged, she zagged and I ended up beaten and bleeding. She smirked, her heel on my chest, and snapped her fingers. I saw a portal to Hell open and she disappeared through it. It closed behind her and I passed out. Next thing I knew I woke up here and here you all are."

"So what you're saying is," Sam asked. "Abbadon is in Hell, and she's…"

"She's waiting for us to make the next move…" Crowley sighed.

"So hold up a second," Dean exclaimed. "You mean that bitch wants us to come to her?!"

"It would appear so Dean." Castiel replied.

"So basically that means…" Kevin gulped, fearing the worst.

"Congratulations," Crowley said sarcastically. "You boys are on the highway to Hell."


	2. Highway To Hell

**Summary for the Chapter:**

> The couples take time to themselves before they're set to leave. Dean and Castiel have part of an important conversation. Crowley helps Team Free Will descend into Hell to go after Abbadon.

Somehow Team Free Will managed to sneak Crowley out of the hospital unnoticed. Well, with a little help from Titan and his angelic doggy powers. The Angelhounds housed the same powers as angels inside them and thus they could do a lot of the same things. With a quick order from Dean Titan wiped clean the memories of the nurses and doctors who'd worked on Crowley and the hospital records of him ever being there. Castiel healed Crowley's injuries and the group snuck off towards the Impala. After reaching the car, Castiel and Gabriel took off flying towards the motel.

"Meet ya there boss." Titan barked once and then disappeared in a split second flash of light.

"That dog gives me the creeps sometimes…"Kevin admitted as he climbed into the back seat of the car and buckled in. Crowley followed in suit and Dean and Sam got in the front.

"Ya get used to him." Dean smiled, drove out of the hospital parking lot, and started off down the road towards the motel room.

"Just wait till you see Hellhounds and I mean actually see them this time," Crowley chuckled, but there was genuine sadness in his voice. "They're nasty suckers, bred for the same reason Angelhounds are, to fight among other things."

"Well at least we've got one thing Abbadon doesn't." Sam chuckled.

"And pray tell what exactly that is?" Crowley asked.

"Hell's most adorable tour guide." Sam replied and Dean and Kevin burst out laughing.

"Oh shut it Moose," Crowley replied. "Lest you forget you were once the devil's cabana boy?"

"Don't remind me." Sam said. "Please."

The rest of the car ride was uneventful. Nobody talked much; they were all caught up in their trains of thought. Sam was regretting even being there. He and Gabriel had been having the time of their, well possibly only Sam's, life and then he was whisked away once again into a hunt, but not just any hunt the second mother of all hunts. Descending into Hell. When Crowley had brought up Lucifer it had left a rancid, bad taste in the younger Winchester's mouth. Lucifer had been redeemed; this was common knowledge now to anyone in the hunter, demon, and angel world. Lucifer wasn't bad anymore. He'd helped to save Heaven, but Sam still couldn't forget the past.

Dean on the other hand was wracking his brain trying to decipher their next endeavor. Hell. He'd been there before, but this time it was going to be different. He'd willingly be marching in head first, like some suicidal adrenaline junkie looking for a high. At least he'd have his boyfriend by his side. Castiel. It felt strange to be calling an angel of the lord his boyfriend; in fact it felt strange to be calling anybody his boyfriend. But that wasn't what had Dean worried. Castiel had been acting so differently ever since he'd regained his 'angel juice' as Dean liked to call it and every time they were in a room together there were so many unsaid words in the air. Dean wanted nothing, but to know that his angel was doing alright. He'd decided to confront him that night before bed.

Kevin's thoughts were quiet; he was just taking it all in. But Crowley, his thoughts were spinning, reeling inside of his head. He'd be entering the domain he'd lost control of, he was fair game. The demons could do anything they pleased to him, anything at all that their little black hearts desired. He didn't control them anymore. That, scared him most of all.

-8-8-8-8-8-8-

When they arrived at the motel room night had fallen and the air had grown chilly. The lights were on in the room before the brothers, Kevin, and Crowley entered and they found Gabriel sitting on the couch flipping through the channels on TV and Castiel aimlessly watching it. Dean set his gun down on the table and shed his jacket before smiling at Castiel and walking over to him. He placed a soft kiss on his cheek and then stood back up.

"Hey Cas." He said quietly. Castiel smiled too, but it wasn't a real one. Another thing to add to Dean's list of worries: An Unhappy Angel. Check!

"I believe it would be best to get a night of rest," Crowley stated. "Hell will be harder to break into then Heaven and it will be far more treacherous and tiring."

"Been there done that." Sam and Dean both mumbled in unison.

"Get some sleep boys," Crowley nodded and motioned towards the door. "I'm gonna check in a room for myself."

"I booked us a room down the hall Sammy," Gabriel said walking over to him and moving some hair from his eyes. "You look tired anyway. C'mon let's go to bed."

Sam was about to protest, but Gabriel's puppy dog look, much similar to his own, won him over. Sam smiled and strolled out the door hand in hand with Gabriel, closing it behind him, leaving Castiel and Dean alone.

"Well uh," Dean tried to make small talk. "I'm gonna take a shower okay?"

"Yes Dean." Castiel nodded and turned his attention back to the cartoons on television. It was Wile E Coyote and Roadrunner again.

"You used to be that coyote Castiel," his thoughts wouldn't shut up. "Always chasing after an absent Father."

Dean's smile faded when Castiel's did. He sighed, grabbed his clothes from a heap on the floor and walked into the bathroom to shower.

-8-8-8-8-8-8-

Running water, the smell of soap, and hot steam filled the air in the bathroom.

"I don't need no one to tell me about Heaven," Sam soaped up his long dark hair and sung. "I look in my daughter and I believe."

"Nice voice Sammy," Gabriel was suddenly in front of him and he jumped. Gabriel smirked at the well toned hunter under the stream of steam. "Ever thought about American Idol?"

"Gabe!" Sam went to cover himself. "I'm naked in the shower and you decide to just pop in! Ever heard of a word called privacy?"

"Oh c'mon Sammy," Gabriel's expression turned more serious, more loving. "I saw every inch of you the past few nights. Every beautiful inch."

He moved Sam's hands away from where they rested and held them in his own, rubbing the backs of them soothingly.

"You don't have to hide yourself from me." Gabriel chuckled lovingly.

"This doesn't make this any less of a privacy invasion." Sam smirked.

"Oh c'mon you're enjoying this." Gabriel smirked back and laughed. The water had completely soaked his head and shoulders as well and the steam made the moment even hotter.

"Unlike you," Sam retorted, washing the soap from his locks as Gabriel watched in amusement. "I don't get off on sneaking into people's showers."

"No," Gabriel snapped his fingers and the water suddenly turned cold. Sam yelped and arched his body forward to avoid the cold water. He was inches from Gabriel. "You get off on me and me alone."

"This was your plan all along wasn't it," Sam played along. "You pervert."

"Not my fault I wanna get ya by the balls again Sam." Gabriel stared into the hunter's hazel eyes and Sam instantly blushed. He felt that familiar pool of heat in his lower stomach.

"Again," Sam tried to compose himself. "You're a pervert."

"You like it." Gabriel pulled him closer and kissed him heatedly, Gabriel snapped his fingers and the water turned warm again.

"You're right," Sam smiled and kissed back. "I do."

-8-8-8-8-8-8-

The lights were turned out and the television was off. Dean held Castiel under the surprisingly warm motel comforter and carded his fingers through the angel's dark hair. Castiel sighed contently and snuggled closer and closer to his lover. Dean placed a small kiss on Castiel's forehead.

"We gotta have a talk Cas." Dean whispered, he didn't know why, it just felt more personal, intimate. They were in a dark room cuddled up together.

"About what Dean?" Castiel asked in a rather unenthusiastic tone.

"You, me," Dean suggested. "Us."

"What about us?" Castiel asked, this time there was a little life in his voice.

"Where are we going from here Cas," Dean said. "I mean after this whole Hell thing is over we're gonna slam those gates for good man. They'll be no demons anymore. Our worst enemy, Heaven's worst enemy. Gone!"

"I don't see your point Dean…" Castiel's voice was monotone, but more than usual.

"We'll be free men Cas," Dean explained. "Sure they'll be a freak monster every now and again, but we'll take care of it. Other than that we can do…anything we want to do Cas. Anything we want to. Actual free will."

Castiel stared blankly at him.

"What do I have to draw you a picture Cas?" Dean threw one of his arms up in the air and chuckled. "We can finally focus on us…so many years after when we finally get together we get thrown this damn monkey wrench. But once this is over with and Abbadon is gone we'll be able to actually be a couple ya know?"

"That would be nice yes." Castiel nodded into Dean's chest and sighed once again.

Dean slid down under the sheets more so he was eye to eye with the angel. Dean moved Castiel's hair back away from his face and touched his cheek comfortingly with the back of his fingers.

"Look Cas," Dean said. "We have to start being honest with each other. What is it you're hiding from me? You can tell me. I'm a big boy and I can take it."

"You can take it Dean," Castiel said. "But you won't."

Dean at first did not catch Castiel's subtle hint. He was clueless; he wracked his thoughts for a moment before realization dawned on him. The angel had gotten better at hinting things over the years.

Castiel wanted to have sex with Dean.

Now Dean wasn't one to deny getting his rocks off. Sure, he'd had many a one night stand to do just that, but this time would be different. It wouldn't be mindless sex with some chick at a bar all for getting off, this would be love making. Something Dean wasn't necessarily that great at doing. He'd only considered it really intimate with Lisa that one time. If this was something Castiel wanted, Dean sure as hell wanted to give it to him.

"You want sex don't you Cas?" Dean asked Castiel. "And you've wanted it for awhile haven't you?"

"Yes but," Castiel said bitterly and turned away from Dean. "Your sex drive was not put into gear for men Dean."

Dean was about to reply, but he stopped himself. In a way Castiel was right. Dean had repressed his attraction for men for so long that he automatically went to women any time he wanted the deed to be done. No matter, after this was all over, he was going to prove Castiel wrong.

-8-8-8-8-8-8-

The night came and went and Team Free Will gathered the next morning in Dean and Castiel's room to begin their journey. Dean had gathered all the necessary ingredients for Crowley's portal spell and was currently busy packing their duffel full of weapons and necessary supplies. He heard a knock on their door and went to open it. Sam and Gabriel entered with two full duffel bags and threw them down next to Dean's.

"Where'd you get that little bro?" Dean smirked and pointed to the clearly visible hickey on Sam's neck.

"None of your beeswax Dean." Sam smacked his hand away.

"We did the horizontal conga for hours on end last night if you must know Dean-o." Gabriel conjured a lollipop and licked it.

"More than I needed to know…" Dean grimaced.

"You asked." Gabriel shrugged and Sam shot him a bitch face.

Soon Crowley arrived and without a word he picked up the bowl and started mixing everything together. He seemed different somehow; more human, more…scared, but Dean didn't comment. Once Crowley chanted a few lines of a spell there was a quivering in the wall and it burst open in a wave of fiery heat and yellow.

"Well?" Crowley asked. "What are we waiting for?"

Dean gulped and looked over at Castiel who nodded and took his hand. Sam did the same with Gabriel, Kevin took a deep breath, and Titan barked confidently as he stood by Dean's side and awaited command. Dean stood stoically and motioned for everyone to follow him through.

"Here goes nothing." He said breathlessly as they all stepped through, the portal closing behind them.

**Notes for the Chapter:**

> Reviews are appreciated!


	3. Descent Into Hell

**Summary for the Chapter:**

> Team Free Will makes their way into Hell. They are faced with their first challenge almost immediately.

The tunnel they'd walked into was dark and dingy. Single flames lit their way, attached to wooden stakes hung on the walls. It was like something out of an Indian Jones movie. Dean chuckled to himself at the thought and kept walking. Titan's hair was standing on end and no matter how many times Dean told him it was going to be alright Titan never relaxed. Dean couldn't expect him to though, or anyone else with them for that matter, they'd just descended into Hell after all.

Dean sensed Castiel's uneasiness, sure they had all been here at least once or at least Dean assumed Gabriel had traveled down here before, but that didn't make the angel any less nervous. Dean took his hand and forced a smile. Castiel looked up at Dean for only a moment before looking down at his feet moving forwards across the dirt in the darkness.

Crowley stoically led the group, humming a familiar tune. Kevin stared all around him shaking a bit with fear; he was the only one of them who hadn't been to Hell before. Titan strolled alongside Dean, but he still whined a bit with every step he took. Sam and Gabriel were hand in hand, gripping each other tight, Sam, not wanting to let go and Gabriel not letting go for the same reason.

"Are you humming Ring of Fire?" Sam asked Crowley, a little bitterness in his voice.

"I thought it was appropriate." Crowley shrugged in reply.

Dean rolled his eyes and kept walking. Castiel let go of his hand and begun to pet Titan. Dean caught up to Gabriel and his brother and placed a hand on Sam's shoulder.

"You okay Sammy?" Dean asked with true concern in his voice.

"Yeah Dean I'll be fine," Sam replied as Gabriel squeezed his hand. "How about you, how are you holding up?"

"I'll be okay," Dean admitted. This time it was going to be different; he wasn't alone in Hell this time. "I've got the A-Team on my side this time."

Sam and Dean both chuckled a bit until Gabriel gave Dean a look that it was time to leave him and Sam alone. Dean quickly got the hint and made his way back to Castiel, Kevin and Titan who were still at the back of the pack. They all walked for a bit before Crowley stopped abruptly and everyone ran into each other behind him.

"What the hell Crowley?" Sam exclaimed. "A little warning next time you're gonna stop would be great!"

"Hush Moose," Crowley was currently staring down two different pathways, both were caked in dark and dirt. "I'm listening. Do you all think you could shut your pie holes for at least a minute while I do so?"

"Rude much?" Gabriel huffed.

"Yeah really." Kevin muttered.

"Don't you dare mention pie." Dean almost actually whined. He wanted so badly to be back on Earth already.

"Would you all be bloody quiet?!" Crowley growled and that silenced everyone.

Everyone tried to listen, but it was something only Crowley and Titan heard. The Angelhound started to growl menacingly and stare off into the distance behind Dean and Castiel. There was nothing there that they could see, but something would probably catch up to them soon. Suddenly the hound let out a high pitched squeal and hopped away from where he was standing. Titan lifted up a paw and inspected it, a black liquid oozed out of the newly created wound.

"What the hell?" Dean exclaimed.

"We have to move now!" Crowley demanded.

"Why?" Sam asked, but suddenly he saw why.

Suddenly, masses upon masses of black scorpions were making their way towards Team Free Will. They all had their tails poised high and they were ready to strike. An ominous giant hiss echoed through the cavern.

"We do need a little protection down here from outsiders or we might get robbed or invaded," Crowley explained fast as he pulled everyone forward. Titan limped, but ran to catch up. "Who else did you think cursed King Tut's tomb?"

"So you're saying we get stung…" Dean gulped. "We die?"

"Move your asses and you won't!" Crowley yelled and took off running down one of the tunnels. Everyone ran as fast as they could, the angels could've flown but they chose to stay at the rear of the group with Titan and occasionally send some angel mojo the scorpions' way. Titan's eyes were glowing white and every time he turned around and barked a blast of angelic power shot from his mouth and at the scorpions. The ones in front were immediately incinerated, but more and more kept coming.

"Where are we going?!" Dean yelled as he ran for his life, he'd had enough of almost dying lately. He'd already been bitten on the ankle, from which he still had a nasty permanent scar, by Titan before Heaven had been restored. He could live without being stung by a big black venomous scorpion, literally.

"It's just up ahead!" Crowley yelled back. "If we can make it to the gorge we'll make it away from them!"

"The gorge?!" Dean exclaimed angrily.

"When I say jump!" Crowley yelled at everyone. "Everybody jump!"

Dean and the others suddenly saw what Crowley had been talking about. It was a tiny gorge, probably leading down to the true underworld. It was wide enough that they could jump across and the scorpions thankfully could not follow them.

"Okay," Crowley took off flying as he jumped across. "Jump!"

Dean paused for a split second, making sure Castiel had caught up and once he saw him and the others he leapt across the ravine. He landed hard on the other side, but he didn't care. Sam jumped next and made it, landing as carefully as he could next to Dean and looking back for his boyfriend. Gabriel quickly flew across to the other side, landing with grace and Castiel did as well. Kevin was the last human to jump and he landed better than the rest of them. Titan barked and then bounded across the way and landed in a heap. He whined and shook as he tried to get up. The scorpions all hissed and spat, but then retreated away once they knew they couldn't make it to the other side. They disappeared back down the path from where they had come and everyone gave a collective sigh of relief.

"Titan," Dean said nervously as he approached the injured Angelhound. "Are you okay buddy? Did they get you?"

"It h-hurts boss…" Titan whined and laid his head down in defeat. He was still alive though, for the time being.

"Angelhounds are designed to withstand Hell's various poisons and such," Gabriel explained as he held Titan's injured paw, inspecting it then standing up again. "He'll survive; he'll just be in a lot of pain until tomorrow."

"We should rest up again," Crowley instructed. "This journey will be long and hard…"

Everyone seemed to let out a groan at his statement.

"And we'll need to all be at full power," Crowley continued. "I'll use the torches in the path up ahead for firewood and we'll sleep."

"Sounds good to me." Dean admitted, still out of breath.

-8-8-8-8-8-8-

After a fire was built Team Free Will and Crowley gathered around it and tried to get warm. Sam and Gabriel were cuddled up together against the wall of the cave and Gabriel was snuggling his face into the crook of Sam's neck. Sam kissed his forehead and then rested his cheek against the top of Gabriel's head as they slept. Dean could've sworn he heard Gabriel chirp like a bird, but he didn't say anything. Dean lay with Castiel, staring at the fire and the flames that were dancing in front of them. Dean ran his fingers through Castiel's hair and the angel sighed contently in his sleep. Somehow Castiel had managed to fall asleep, but Dean knew he'd be awake for awhile. It was too nerve wracking to sleep in Hell. Kevin had surprisingly conked out as well, Titan by his side. The boy and the Angelhound were both out cold and Dean smiled. He found the scene almost cute.

Crowley sat alone against the wall and stared at the fire like Dean had been doing. He solemnly looked forward. Dean carefully laid Castiel down so as not to wake him and walked over to the ex-demon.

"You should've called earlier," he kept his voice low. "Once you knew you were on Abbadon's trail. I would've helped you."

"She got the jump on me squirrel," Crowley chuckled and Dean sat down next to him. "And now she won't know what bloody hit her when we're done with her."

"Must feel strange," Dean commented, looking up at the ceiling then back to Crowley. "Being back here, without ruling these paths?"

"I'll admit it feels off," Crowley replied. "But strange? Not any stranger than usual. Lucifer and I both have walked this dirt enough times to know it forwards and backwards, but…"

"But now," Dean finished for him. "You're without powers and you're scared."

"That's one way of putting it." Crowley sighed.

There was a lull in the conversation.

"Look Dean," Crowley sighed. "When I said I'd lost people I meant it, I've lost a few people I really did care about to this witch and other evils. I just wish for this all to be over. These next six Realms of Hell will be trying…"

"Oh great the Realms thing again." Dean rolled his eyes.

"There's only six this time," Crowley smirked. "So be happy. Anyway, they'll be trying and I can't guarantee that any of us will make it to the end and out alive, myself included, so I guess what I'm trying is don't be like me and keep your loved ones close."

"He'd be proud of you ya know?" Dean smiled. Somehow he knew exactly who Crowley was speaking of. "For helping this messed up world and not just for you. He'd be glad you stopped being such a demon."

"Bobby Singer was the greatest man I ever met," Crowley said, not mentioning a word about what exactly their relation had been, although Dean could take a pretty good guess. "I'm doing this for him as well. This is what he would've wanted. Retribution for the world and his sons."

Dean nodded in appreciation of the points Crowley had brought up and leaned back against the wall. He looked back to the flames as he watched his friends rest. The next day would most indeed be a thrill ride.

**Notes for the Chapter:**

> Reviews are appreciated!


	4. The River Styx

**Summary for the Chapter:**

> Team Free Will makes their way into the First Realm of Hell: The River Styx. Dean makes a potential grave mistake which may cost Team Free Will time and could've have cost him, his life.

When Team Free Will awoke the fire had burned out and they were once again shrouded in darkness. Crowley stuck a hand out to reassure them and guided them towards the nearby tunnel which, thankfully, was lit up by torches. Every bone in Dean's body screamed in a mixture of pain from lying on the hard dirt all night and anguish about what was to come. Every fiber of his being warned him that this might be it this time, this time they might die. Hell was a lot more unforgiving than Heaven, if they rubbed someone the wrong way or their foot slipped climbing a wall of rock and dried mud they were goners. There were no second chances in a place which thrived on death and misfortune.

"There are Six Realms," Crowley explained to everyone who hadn't heard his conversation with Dean the previous night. "They are similar to Heaven's, but not quite the same. You may have thought you were safe just cuz you were Heaven's little heroes. Let me be the first but certainly not the last to tell you that you are wrong. Hell's residents will not care about you or pity you in any way do you understand me? They'd rather have your head on a stake. Stick with me and there's a chance that you may live."

Dean took Castiel's hand in his, memorizing its very texture down to every line in his palm. He didn't know if he'd feel it ever again after they undertook these Realms. Their options weren't looking too good at the moment.

Crowley nodded once and looked around before leading them down the darkened tunnel.

-8-8-8-8-8-8-

After awhile the heat increased a bit and there was this smell, this horrible smell, it reeked of death and pestilence. Dean swallowed hard, trying to keep the small amount of contents in his stomach, well, in his stomach. Castiel gulped once, Dean could tell he was trying hard as well. Sam had covered his mouth and nose, as had Gabriel and Kevin. Titan leaned his head away, but kept walking forward. Crowley seemed unaffected by whatever it was. He didn't even grimace once. Dean had to admire his ignorance of the smell, not to mention the emotional effect, whatever this was, was having on Dean and surely the others. Although, Dean forgot for a moment that he had spent most of his life down here.

"Welcome to the First Realm," Crowley said with a small, sarcastic smile. "The River Styx."

"Renegade you had it made…" Dean heard Titan sort of recite more than sing the lyrics to 'Renegade' by Styx through his thoughts and Dean glared at the hound who whined in response. "Sorry boss I thought it was fitting."

"That dog of yours I swear." Gabriel rolled his eyes.

"This," Crowley interrupted. "Will probably be the most painful of all the Realms, although I can make no guarantees."

"Wait this is the River Styx," Sam exclaimed in surprise. If they hadn't been on a potential death mission, his nerdy side would've been more interested in the piece of history before them. "As in Greek and Roman history River Styx, as in souls of the damned River Styx?!"

"No," Crowley sarcastically replied. "The one in Disneyland…"

"Look Crowley," Kevin said. "Don't be a smart ass. Just tell us how to get across…"

"It's simple really," Crowley said. "You swim across and hope to dear whomever above or below you believe in that the pain doesn't kill you first."

"Sounds positively delightful." Castiel replied. It was filled with sarcasm.

"Just try not to let it mess with you," Crowley instructed. "The thoughts it can conjure up could kill you before the physical pain ever did, a little known fact by the Greeks and Romans and no Achilles did NOT become invincible in the River, his mother made a deal, that's one that'll give all the history teachers heart attacks."

"I'll go first," Gabriel volunteered. "It'll go easy on angels."

"Oh please you could just fly over," Kevin scoffed. "You and Cas both!"

"Actually there is a barrier," Crowley explained. "It keeps anyone from passing by air. I did not make it, but it's a nice touch."

"Shouldn't Crowley go first," Castiel glared a little, he still felt a bit deceived by the ex-demon. "To prove his loyalty?"

"To whom?" Crowley asked defensively. "To Hell? Because those days are over. I just want this all to end!"

"Alright break it up you two!" Dean yelled pushing them a good distance away from one another before either one could do anything. "I'll go first!"

"Dean, no…" Castiel's voice came out rather soft.

"What harm could it possibly do to me?" Dean asked. "I've been down here once before, I'll be damned all over again if I'll let a puny little river kick my ass!"

"It's your funeral," Crowley said. "I mean choice. As they say, pain lies on the riverside. The water runs deep and the banks run dry."

Dean huffed and walked over to the water's edge. He didn't see much to it. The water didn't look too terribly deep. Although it was a murky dark black and he couldn't even see the bottom. Dean swallowed a lump forming in his throat and took off his leather jacket, giving it Sam to hold before returning to the edge. He paused a moment and looked back at his friends, he stared at Castiel the longest before turning back around and taking the plunge into the darkened depths below.

-8-8-8-8-8-8-

Searing white hot pain. It was all Dean felt. He held his breath hoping one gulp of air would last until he resurfaced. He didn't even feel wet, it was as if the river had wrapped him in an embrace and was refusing to let go. He almost felt suffocated. His lungs felt as if they were going to burst and his heart was pounding faster than it should.

Dean kicked and swam through the water's depths as fast as he could and only moving forward. He hoped to reach the other side before he ran out of breath. He freaked out and let out a few breaths of air only when the hand of a damned soul reached out and touched his arm. Dean pushed the water around his arm away and the soul disappeared. Fire, his lungs, they were on fire.

More fire, pain in his lungs, and white behind his vision. Dean couldn't take much more. He was seeing thing too as if it wasn't enough pain. He saw his mother and father, but both deteriorated before he could reach out and touch them. He saw Sam and Kevin and Crowley, he saw everyone. The water was playing tricks on him and somehow deep in his gut he knew it. He saw the past, memories long since buried. The present day was easy to see, but the future that was what hit Dean in the heart.

He saw himself and Castiel. He saw Castiel lying in bed and he looked over at him, lying next to him. Castiel smiled back and looked down at the end of the bed. There sat two young excited children, a boy and a girl both with Dean's eyes and Castiel's hair. They were probably at least seven or eight years old. They bounced happily on the bed and Castiel and Dean. Dean had the biggest smile on his face and his and Castiel's ghostly laughter echoed in the murkiness.

Dean couldn't, wouldn't have that. The water was taking him slowly. He felt his mind turning to mush. His vision was borderline gone and foggy. The water burned his skin and his insides. He finally had to open his mouth and he screamed. The water absorbed the noise, but Dean screamed with all that was left in his lungs. The water flooded his insides and he begun to drown.

After awhile he felt like a rag doll. There was nothing left of him to even begin to push him back up to the surface. Dean felt weightless like a cloud and then he became comfortably numb. He drifted downwards into darkness.

-8-8-8-8-8-8-

"I heard him groan a tiny bit that's a good sign isn't it?" Kevin exclaimed.

"Give him some air, Gabe just mojoed him guys." Sam instructed, still worried.

"I bloody swear he's nuts." Crowley retorted.

Titan barked.

Dean coughed. He coughed hard. Gallons of water, it seemed, poured out of his mouth and below him. The searing pain was gone and the memories and visions, the voices, all silenced and gone. He saw only white at first, but after awhile his vision cleared and he looked up to see all of Team Free Will and Titan staring at him. Dean sputtered and sat up fast, coughing and gagging on the liquid left in his throat and lungs, which surprisingly wasn't very much.

He felt the ground underneath him only to find it in fact was not ground…it was wood. Dean felt up the wood around him and looked on either side of where he was seated. They were on a boat. A rickety old boat, but a boat none the less.

"You swallowed half the souls down there," Crowley joked a bit and leaned back against the side of the wood. "Are you alright?"

"Well hmm let's see you son of a bitch," Dean growled. "I almost died down there and you couldn't bother to tell me there was a damn boat!"

"I honestly thought it was out of commission since Abbadon took over," Crowley whistled a bit. "And I honestly didn't expect you to jump dive right in there like that, but I guess they do say "only fools rush in"?"

Dean went to punch him, but he then felt Castiel's hands on his arm. He stared up at his angel whose eyes said 'just let it go'. Dean sighed, gathered his bearings, and sat up with Castiel against the side of the boat.

"Titan saved your ass," Gabriel stated. "He had to dive right in and pull you up about maybe fifty feet to this boat? Pretty impressive for a mutt of Balthazar's."

Titan growled and then sat down protectively next to Dean. He poked his nose in between him and Castiel's hands and licked Dean's fingers.

"Thanks Titan." Dean smiled and petted the hound's head.

"No problem boss." If it was possible, Dean could have sworn Titan was smiling.

"So whose boat is this?" Dean laughed. "Gilligan's island gone wrong?"

"Oh this boat," Crowley pointed to their captain who stood currently at the head of the boat who didn't look much older than nineteen, he was wearing all black clothing, a tight shirt, skinny jeans and Doc Martin boots. He had jet black hair of average length and eyeliner under his eyes, either that or he was really hung over. That was Dean's other possible conclusion. He had diamond studs in both his ears. He didn't smile much, but in such a dismal place Dean didn't expect him to. "This is the epitome of Charon himself."

"Oh please," the teenager said as he pushed the boat along. "Charon is unfortunately my old man, my name is Ron."

"Charon, the deliverer of souls is your dad?" Kevin asked.

"Yeah," Ron shrugged. "Not the best family business I know, but I can't imagine anything worse than down here."

"Try doing our jobs Ron," Sam chuckled. "Then we'll do yours and compare notes."

Ron smirked before turning back forward and rowing some more.

"We should reach the Second Realm in record time now because of this," Crowley said. "Until I'd suggest resting up again."

Dean and the others didn't have to be asked twice.

**Notes for the Chapter:**

> Reviews are appreciated!


	5. Boat Rides and Realms

**Summary for the Chapter:**

> Ron Ryder, Son of Charon provides Team Free Will a ride to the next Realm of Hell: Soul Asylum. Once there, a little mishap leads Dean and the rest of Team Free Will to an ally down under.

The rest of the boat ride was pretty uneventful. It mainly consisted of sleeping, occasional seasickness (it turned out Jimmy Novak hadn't done too well on boats, which was unfortunate for Castiel), and Crowley regaling tales of people who'd sold their souls for various incredible feats.

"Oh yes, many, many presidents," Crowley listed off. "Buzz Aldrin like I told you, oh and you didn't think Shakespeare wrote all those plays all by himself without some help did you?"

It was interesting learning the real means behind some historic moments and figures, but Dean couldn't focus on that. He was too worried about the Second Realm and all the ones that followed. Hell was an incredibly dangerous place and he hated to see his family, those he cared about most, susceptible to what it had to offer in its deepest depths. Titan whined and shifted into a new position on the floor of the boat. Dean could sense his boredom and wariness as if he could sense what was ahead and he probably could.

"It'll be okay buddy," Dean petted him and Titan let out a sigh, he then turned to Castiel who was leaning halfway out of the boat, hand on his stomach, and looking rather pale. "How you holding up Cas?"

Dean crawled over to the angel and leaned against him, holding him steady. Castiel groaned a little and leaned his clammy cheek against Dean's warm chest.

"You can fly and be fine," Dean chuckled. "But you're motion sick?"

"Don't talk…" Castiel grumbled. "For some reason it makes it worse…"

"Gee thanks." Dean laughed and kissed his forehead. "Don't worry Cas, we'll be there soon then maybe you can rest."

"My inner gastro intestines cannot handle much more of this Dean." Castiel moaned and held his stomach as he again retched off the side of the boat. Nothing came up and he mostly gagged, but it still looked painful. Castiel sat back down next to Dean and whimpered. Dean sighed.

"Hey Ron," Dean said. "You got any saltines or something like that?"

"Why didn't you just ask?" Ron hopped down from his perch and handed Kevin the steering stick. "Think you can handle this for me?"

Kevin was a little shocked, but he immediately starting rowing as if he'd done it all of his life. Ron winked at him and Kevin immediately this heat building up in his cheeks. He didn't know what was wrong with him. He'd just met the Son of Charon, why was he reacting the way he was? Ron made his way over to the back of the boat and pulled out various things. He tossed Dean a ginger ale and some crackers and a package of motion sickness pills. 

"Normally my dad would tell his passengers to just suck it up," Ron explained. "But I don't roll that way. You should've told me earlier he was getting sick and I would've given you all this shit a long time ago."

"Thanks Ron." Dena nodded and Ron ran back to his position at the front of the boat. He took the stick from a confused Kevin and continued steering them along. "Alright Cas I know this doesn't look all that great right now, but it'll help your stomach I promise."

"O-Okay Dean…" Castiel whined and Dean popped the lid on the ginger ale, some of the golden liquid spilled onto his fingers and he licked it before holding the can up to Castiel's lips.

"Alright now drink slowly," Dean instructed. "And have a few crackers afterwards, but eat them slowly too. If you eat too fast you'll get sick again okay?"

Sam smiled at the scene. It was almost cute how Dean took care of Castiel like that. It was like something out of a Hallmark special and normally things like that, they made Sam feel ill. This was different. This was his brother, happy and that wasn't sickening at all. That was all Sam wanted for him. Sam looked over at Gabriel who was staring off into the water longingly. Sam scooted closer to the archangel and took his hand before pulling him into his arms and kissing his cheek.

"What is it Gabe?" Sam asked him. He kissed him twice on the lips, slowly and softly. Gabriel kissed back but sighed.

"Nothing Sammy." Gabriel said.

"Oh c'mon," Sam protested. "It can't be nothing if you've got such a long face."

"It's just," Gabriel sighed again, there were tears brimming in the corners of his eyes. "Crowley said we might not all survive. I just got you back Sammy, I'd been gone for so long. This lifestyle, hell this life. It's hard. I just…I saw a future with you Sammy I still do. I don't want Abbadon to take that away."

He started crying a little as he whispered the last part.

"I don't want anyone taking that away…" he choked.

"Oh Gabe," Sam sighed and pulled him close. "Look at me okay? Look at me."

Sam cupped his cheeks and wiped the tears that had begun to fall with his thumbs. Gabriel's lip quivered a little.

"I'm supposed to be the strong one Sammy," Gabriel sniffled. "I'm the archangel; I'm Heaven's most powerful weapon. I-I'm supposed to be fearless and r-right now…I-I'm scared outta my wits kid…"

"I know Gabe," Sam whispered in his ear as he hugged his boyfriend. "I'm scared too."

Sam didn't say another word. He just held Gabriel. He held back the tears that threatened to spill from his eyes as well. Now was not the time to cry. They couldn't, they wouldn't, give up. Sam would have his happy ending damn it and so would Dean and Kevin and even Crowley. This would end. They would be happy.

They would be safe and they would be happy.

-8-8-8-8-8-8-

As Ron rowed them into port a feeling of deep uneasiness settled in Dean's gut. He knew now why many people had named it Hell. He heard the screams, the blood curdling screams of souls. Damned and tortured souls surrounded him and not just in the water, but in the air, in the dark corners of the pit, everywhere. He could feel their despair in his bones and honestly it terrified him.

"Welcome to the Second Realm," Ron said. "Soul Asylum."

"Do you and Heaven have some I don't know thing going on where you name everything after old eighties songs?" Dean asked.

"You're forgetting many singers are Prophets Dean." Castiel croaked out and shakily sat up as the boat turned towards the dock.

"Or demons." Crowley said and stood up. "Unfortunately Ron can only take us this far so please thank him for his lovely assistance and get a move on. We have four more Realms to get to."

"Thanks Ron." Dean nodded and helped Castiel to his feet. Dean and Titan both held the angel steady as he walked down the wooden dock and towards dry land.

"Land," Castiel murmured. "I could kiss it right now."

Dean laughed.

"Yeah thanks Ron." Kevin said, smiling at him. Ron winked again and handed Kevin a piece of paper with a phone number on it. Kevin was confused at first, he'd brought his phone sure, but he doubted he'd even have service in Hell.

"You need me you call me you got that? Trust me that phone of yours from the human world? It'll work down here." Ron said and started to lift anchor.

"Thanks." Kevin said as the teenage boat driver pushed off and started back downstream. Kevin stared at the Son of Charon for a few moments before he pocketed the piece of paper he'd given him and walked over towards Sam and Gabriel who were standing a bit farther away from the group and comforting each other. Sam had his hand in Gabriel's and he ruffled some of his golden blonde hair with the other. Gabriel pressed his body into Sam's chest and sighed. Dean was holding onto Castiel who looked a hell of a lot less green than before and had actually regained all of his color and balance. Crowley stood next to Titan who still seemed a bit rigid in his presence. Kevin could only presume it was because his kind and Titan's kind had been enemies for years.

"We should hurry." Crowley said and pointed to the doors leading to the supposed asylum. "The faster we get to Abbadon, the faster we get home."

Crowley started off down the path and Kevin followed a close second. Titan looked back to Dean before taking off after them. Dean nodded at his hound and he and Castiel both walked through the doors after. Sam and Gabriel were the last to enter before the doors to Soul Asylum shut behind them with a low and rusty groan.

-8-8-8-8-8-8-

"This was where I rescued Bobby from," Sam explained to Dean. "When I did the second trial. He was in one of these cells…"

Dean nodded. He hadn't really said a word since they'd entered. The screaming of souls had been enough for him to hold his tongue. Castiel held his hand tight in Dean's and refused to let go. Crowley walked by each cell, unaffected by the cries emitted and the hands that reached out towards him and asked for help.

"You're here for a bloody reason," Crowley would reply to each one. "Ya hooligans!"

Titan growled and his hackles stood on end. There was so much death around him, Dean could only assume it was driving him to madness not to attack.

Suddenly though, a sinister sounding laugh was heard and a cold chill ran up everyone's spines, even Crowley's. Crowley turned around and then back forward, pausing and taking a breath before it was knocked out of him by an unseen force. Everyone jumped back as Crowley was pressed to the wall and another round of laughs was heard.

"Well," the voice of a demon was heard and soon he stepped from the shadows along with one other one. "If it isn't Heaven's most adorable heroes. Did you really think this would be easy?"

"Honestly we were kind of hoping yes." Kevin gulped.

"Well you're wrong," the other demon smiled and hissed and Kevin felt like he was going to wet his pants a little. He'd seen demons on earth and wasn't scared of them, but they weren't nearly this morbid and creepy looking. "You see Abbadon sent us to just say hello. She's been expecting you all. Especially you Dean Winchester."

"Oh lucky me." Dean said in a snarky reply. "She sent tweedle dee and tweedle dumb as the welcoming committee."

"You make jokes now Dean Winchester," one of the demons said, drawing closer and closer to him. "But Abbadon will take you down one way or another. She just prefers not to get her nails dirty so she sent us."

"So she sends her blind in the dark lackeys to do her dirty work," Dean smirked. "Some villain she is."

"Oh please we were spawned in the dark," one demon smirked back. "The only ones who are going to be blind in this situation…"

The demon snapped his fingers and all the torches blew out one by one leaving Team Free Will, the souls, and the demons in nothing but total darkness.

"Is you…" the demon laughed evilly and Dean gulped.

"Everybody run!" Crowley yelled and everyone took off in different directions. Dean, Titan and Castiel stayed together running down every pathway they could find. Sam and Gabriel had taken off another way as had Kevin and Crowley.

"Stay with me Cas!" Dean instructed. Castiel didn't reply, but he kept a tight hold on Dean's hand as they ran. Eventually they reached a split in the pathways that much Dean could tell by the echoes of their feet, but he couldn't see a damn thing.

"You must die Dean Winchester!" both demons hissed from somewhere. Dean panted hard from running and took off down a pathway. He ran and ran with Titan by his side until it reached its end. He had been running so fast and hard he hadn't even noticed that Castiel was no longer with him.

"Cas," Dean breathed out and then he yelled. "Cas!"

Titan whined and eventually Dean heard the shriek of the two demons they'd been up against and then the lights came back on, most likely the work of Crowley. Dean's chest heaved with every breath he took, but those breaths were shortened when he looked up and saw Castiel staring at him.

"Cas," Dean ran over to him, not paying much attention to anything else. "Damn it man, do not do that ever again! I thought you were dead!"

Dean begun kissing him out of pure fear that if he didn't Castiel would be taken away again into the darkness. It wasn't until he felt himself being pushed away that Dean stopped.

"Ah man what the hell?!" Castiel exclaimed.

"Cas," Dean looked thoroughly confused. "What the hell? It's me, Dean! What's wrong with you?"

"Dean…" Dean heard a voice behind him and looked behind him to see Castiel clearly worn out from running and sweating a little. "I am sorry I lost you, I got separated when we reached the split in the paths."

"Cas," Dean breathed out and looked at either side of him. Beside him on both sides stood…Castiel. This was impossible. "But you, you're over there…"

Dean pointed to the Castiel he'd just kissed and that Castiel was still wiping his mouth from it. He looked up at the other Castiel and jumped.

"Castiel…" he said. "Good to see you again."

"As it is you," Castiel bowed his head a little. "Jimmy."

"Jimmy," Dean exclaimed. "As in Jimmy Novak?!"

"It would appear so." Castiel nodded and looked over towards Jimmy again who was now staring at Dean as well.

"Well," Dean stood up; he looked about ready to pass out. "This has been sufficiently awkward…"

**Notes for the Chapter:**

> Reviews are appreciated!


	6. Hellhounds

**Summary for the Chapter:**

> After a slight mix up in the caves, Team Free Will recruits Jimmy Novak onto their team. They make their way to the Third Realm of Hell: The Hellhounds Realm. Also Titan reveals a useful secret/power to Dean.

"Now hold on a sec," Dean swallowed hard. "Jimmy Novak is dead. But what is he doing here in Hell? If remember correctly Cas, you spared him?"

"Listen Dean I can explain on the way," Jimmy looked around. "But right now we have to get out of here before those demons come back or more like them."

Dean turned his back to Jimmy for a split second before unsheathing Ruby's knife and pointing it at him. He backed up, shocked and surprised.

"How do we know you're not a demon?" Dean exclaimed.

"You don't," Jimmy said, a stone cold look in his eyes. "But Castiel does. He knows why I'm here no doubt and that I'm paying for my sin. In the meantime, however; we need to get out of here now!"

"We can trust him Dean." Castiel nodded and put his hand on Dean's shoulder. The hunter looked at both doppelgangers, sighed, and strolled back down the path from whence he, Titan, and Castiel had come. Jimmy sighed as well and walked away with them, but not before giving one last parting glance to the walls around him.

-8-8-8-8-8-8-

"Please tell me this is one of your jokes Gabriel…" Sam stared at the double image before him of Jimmy and Castiel.

"I'd like to say this is my handiwork Sammy," Gabriel chuckled. "But it's not."

"How do we know he's not a demon—" Kevin started to say.

"We've been over this already," Jimmy interrupted sort of sassy-like. "I'm just a soul, there's nothing demonic inside me."

Jimmy's mannerisms, some were uniquely human and his own, others he shared with Castiel like they were one in the same. Dean figured it must have been a whole new level of strange for Jimmy to be standing next to his physical body and not be in it. Talk about a whole new level of astral projection. They were exact copies, down to every freckle and blemish. In a way it was kind of creepy.

"I heard it through the grapevine that you all are trying to get to Hell's epicenter," Jimmy said. "Pretty impressive I must say."

"No offense Novak," Gabriel retorted. "But what all have you heard through this grapevine of demonic gossip?"

"Nothing too detailed," Jimmy explained "Just that the heroes of Heaven found God and saved the world. Nothing major ya know just the fate of the world."

"All in a day's work." Kevin laughed. He shut up after everyone stared at him. Kevin sighed a little. At least Ron hadn't dogged on him when they'd met. Kevin had decided Ron was a pretty stand up guy. His fingers played with the slip of paper in his pocket with Ron's number written on it. Was there even cell phone service in Hell?

"Anyways," Jimmy blew air out of his cheeks. "I've been wandering the Second Realm in the shadows hiding for awhile, trying to escape. See if you break free and make it out it's hard for them to find you or so I've heard. I finally heard of your arrival and man how I could resist not helping a free ticket out."

Castiel suddenly slammed Jimmy into the nearby wall so hard it shook a little and some dirt came loose and fell to the ground.

"Hell may have excavated its ways into your head James Novak," Castiel's eyes went white menacingly. "But if you expect to just tag along with our group like some lost puppy with sick, demented thoughts then you have another think coming! We are here to kill Abbadon, we are here to get home safely, we are not here, however; to be glorified babysitters for a poor lost soul who once used to be a respected man at least in Heaven's eyes. Do I make these terms clear?"

"Y-Yes Castiel." Jimmy gulped and Castiel's eyes went back to normal before he stepped back, allowing Jimmy freedom from the wall.

"Damn Cas," Dean chuckled, truth be told whenever Castiel went all 'Warrior Angel', as Dean called it, Dean got a little hot and bothered. "You tell him."

"Are we going to just stand here debating this," Kevin said. "Or are we gonna get a move on?"

Everyone was a bit shocked by the Prophet's outburst, but stopped their bickering and obeyed his word. They all started off in the direction that Crowley told them to. The air became heavy again and it actually became a little hard to breathe. Dean's throat burned, he knew right then that they were entering yet another Realm.

"Welcome to Realm Three," Crowley said. "The Hellhound's Realm."

"Oh joy." Dean rolled his eyes. "Another round of mutts to bite my ankle. No offense Titan…"

"None taken boss." Titan barked.

"Sssh," Crowley silenced the hound and Titan let out a small, quiet growl. "Do you want them to know you're here?"

"It's not like they can attack us anyway right?" Kevin said. "I mean we haven't made any deals."

"Actually you are on their turf now boy," Crowley replied. "They'll attack if they can sense you."

"Sense us?" Sam asked.

"Hellhounds are actually practically blind in their home lands because the fires burn at such a high temperature in the places they train so the embers and smoke burns their eyes. They are actually more dangerous on earth."

"Oh goody," Gabriel sarcastically clapped his hands together. "Just what they needed, live bait!"

Team Free Will and Jimmy suddenly held their breath. There, before them was a field of hundreds of Hellhounds all sniffing the grass and some were sleeping. Dean gulped and felt his stomach in his feet.

"So," he whispered. "How exactly do we get around Scooby Doo times a hundred over there?"

"Easy," Crowley hissed. "Quietly and carefully and don't be pea brains about it."

"Don't be a pea brain," Kevin repeated to himself, carefully tiptoeing around even though his heart was beating a million miles a minute if that were at all possible. "Got it, pea brain-ism is gone, kaput, goodbye to it."

"Kevin…" Crowley said with an annoyed look.

"Yeah?" Kevin asked.

"Shut up." Crowley said and continued quietly walking across the grassy field.

"Right." Kevin nodded. "Shutting up, got it."

Dean and Castiel walked gingerly across the grass. Titan resisted the urge not to snap every Hellhound's neck all around him. Dean would've reached out and petted his head, but he was too focused on not being seen by the giant black masses of hounds surrounding Team Free Will.

There was a small crack heard and all of the Hellhound's heads shot up. They all simultaneously growled and inched forward ever so slightly on Team Free Will. Crowley shot a glare back at Kevin who had stepped on a stick in the field and broken it in two.

"Sorry." He chuckled nervously and gulped as he backed away.

"Well gee this scene looks familiar." Gabriel let out a wise crack.

"I take it we should run now!" Dean exclaimed and then Team Free Will took off away from a pack of Hellhounds that had decided to pursue them. They were large black wolf-like dogs with snarling teeth and frothing drool dripping down their muzzles. They were right on the heels of Team Free Will and none of them dared to even look back. Dean jumped over a nearby log and stumbled when he reached the other side, but they managed to start descending into a dismal looking forest. Dean looked back only once to meet the eyes of one of the devilish dogs jumping over the log, but not before Titan's jaw latched itself firmly on the Hellhound's muzzle, knocking him to the ground, and he let out a loud painful whine. Titan growled loudly and snapped and bit at the hound. The hound challenged him and raised its hackles to appear bigger.

The next thing Dean saw he was sure he was imagining. He could've sworn he'd seen Titan smirk, honest to goodness smirk. Then Dean knew he was crazy because standing in Titan's place afterwards was a skinny blonde haired and blue eyed, man. The man let out a growl and the Hellhound backed away in fear, jumping back over the log and running away in the other direction. The others followed behind him and no others seemed to follow.

"Well that was easy wasn't it boss?" the man turned to Dean who stood in shock. "What is there something in my fangs?"

"Okay things are just getting creepier and creepier around here," Dean rubbed the back of his neck and gave the man a 'what the hell' look. "Who are you and what did you do with my Angelhound?"

"C'mon boss you're not that stupid," the man smirked a toothy grin again and when he did it revealed a row of perfectly white teeth. A ray of light flashed through his eyes. "I am your Angelhound. It's me, Titan."

"Okay maybe I'm not stupid," Dean pointed his finger at the boy. "But I'm pretty sure I am going insane."

"It's true Dean," Castiel said, coming up from behind him. "That is Titan. Angelhounds possess the power to shape shift into humans if they need to. They all have a human form as well in case it's needed."

"Alright then." Dean smiled and started off down the path.

The man, Titan, rolled his eyes and shifted back into his Angelhound form before running off in front of Dean.

"Sheesh," he barked, then went back to his master's side. "Tough crowd."

Castiel smirked and started after them. The rest of Team Free Will was already entering the dark forest. Unknown to them though, many pairs of looming evil eyes were diligently watching among the trees. The demons of the Realms had been ordered by Abbadon to keep an eye on her unwanted guests throughout their journey and so far they had much to report to the new Queen.

"Oh yes, Queen Abbadon will be pleased greatly about this." A demon hissed and then disappeared with the others into the black.

**Notes for the Chapter:**

> Reviews are appreciated!


	7. Demontown

**Summary for the Chapter:**

> Team Free Will enters the next Realm of Hell: Demontown. Once again, they're faced with danger at every turn, but they are greeted by another potential ally.

The smell of death and decay was all over once again and Dean almost choked on his own breath. They were getting closer and closer to the next Realm and closer to facing Abbadon head to head. The deeper they'd traveled into Hell, the more the air burned their lungs and the more memories resurfaced for Dean. He could see that Sam was remembering as well. He watched as Gabriel looked up sympathetically at the taller man and took his hand, squeezing it gently. Dean reached out aimlessly for Castiel's invisible hand. Castiel was no longer by his side and was trailing the pack, speaking in a hushed voice with Jimmy. Dean sighed and turned to Titan.

"You're not gonna wig out on me and go human again are you?" Dean chuckled.

"Why?" Titan barked. "Do you want me to hold your hand sweetheart?"

"Very funny wise guy," Dean laughed. "Nah I think I'm good."

"Suit yourself," Titan barked again. "But I swear if you try to give me a damn milk bone I will kick your ass."

"I see my language is rubbing off on you." Dean smirked, he'd learned quite fast the hound couldn't stand dog jokes.

"It's catching." Titan, Dean could've sworn he smirked, ran off towards the front of the group taking his place beside Gabriel. The archangel petted his ears and Dean smiled.

Meanwhile, at the back of the pack, Jimmy and Castiel were discussing everything that had happened since Jimmy's spiritual death.

"You were an honest man James," Castiel stated. "I can ask my Father for your redemption if you'd like."

"I slept with a demon Castiel," Jimmy sighed. "Willingly, I don't deserve it."

"What happened exactly?" Castiel asked.

"After you all left once I was dead and you had my meat suit so to speak, I wandered the earth for awhile. I was lost. I tried to find my wife and daughter somewhere in the veil, but I discovered something far worse. They were gone forever and moved on with their lives. I left town and wandered some more. I met a woman who claimed she'd take me to the other side and that she knew how to get there. I don't know why I believed her, but I did. One thing led to another that evening and I sinned with her. I found out she was a demon when she wouldn't take me to Heaven. I regret it to this very day."

"As long as you're living with your mistake," Castiel said. "All in all you're a good man James Novak."

"We shall see," Jimmy chuckled. "So what about you and Dean? When did this happen?"

Jimmy smirked and Castiel's face turned red. Castiel hadn't really talked much about him and Dean's new-found relationship. Sam knew, Gabriel knew, Kevin knew, and that was alright but Dean had yet to go public with it. Although Castiel was thankful that Dean would willingly, openly kiss him if the desire arose, as shown by the incident with Jimmy.

"After conquering the Realms in Heaven," Castiel explained. "Dean and I were celebrating with our family and I walked outside. Dean came out with me and sat down on the hood of his car where I was sitting. We talked awhile about Heaven and everything that had happened and then eventually he kissed me. It felt so pure; at first I didn't believe it."

"Why not?" Jimmy asked.

"I've loved him for so long, since I rescued him from Perdition," Castiel said. "I could always sense something in him when he looked at me, but until now I was new to emotions and I didn't know what he was feeling. I didn't even know what I was feeling. But now I do and I know that I love him."

"Don't look now Castiel," Jimmy patted him on the back. "But I think you've found 'the one'."

"The one?" Castiel questioned.

"The one you'd do anything for and vise versa," Jimmy explained. "The Romeo to your Juliet, your superman."

"My mate for life?" Castiel asked, still a little confused on what Jimmy was implying.

"If that's what you angels like to call it," Jimmy looked forward at Dean's back. "Hold onto that one Castiel. He's a keeper."

"We're entering the Fourth Realm," Crowley interrupted. "Demontown."

They all paused and stopped for a moment. Gabriel stretched and strolled over to Crowley, whispering something in his ear and looking over to Castiel. Gabriel gave him a curt nod and Castiel gave one back. He looked down at Titan, who had moved next to him, spoke something to him in Enochian and the hound's eyes lit up before he changed into his human form. Dean and the others jumped a little from shock.

"An angel or an Angelhound will stick out like a sore thumb in a Realm full of demons," Castiel explained. "That is why we three will have to be as inconspicuous as possible."

Then a ray of light shot out through the cavern and every human shielded their eyes. When they all looked again Castiel had been replaced by a human sized hawk. The hawk had tawny brown feathers with black on the tips. It had piercing blue eyes which stared into Dean's with a stern gate, but not deadly in any way. The hawk looked over towards Gabriel and where Gabriel had been, a fox, probably the size of Titan's Angelhound form stood with them.

"Demons are not allowed to touch us in our spirit guide forms," Gabriel explained and everyone heard him through their minds as they normally did with Titan. "It's the supreme law of the land in Heaven, on earth, and in Hell."

"We are considered to be in a peaceful state while in these forms," Castiel said through their minds as well. "And not to be hostile, we can fight and defend in these forms, but only if we need to."

"So you become a fox," Sam pointed to Gabriel and then to Castiel. "And you become a hawk?"

"Pretty much Samsquatch." Gabriel said.

They all started walking towards the Fourth Realm. Gabriel and Titan lead the way while hawk Castiel waddled behind Dean and Jimmy. Sam, Kevin, and Crowley followed close behind fox Gabriel.

"What does the fox say…?" Kevin chuckled and mumble-sang.

"I will smite you so hard your grandchildren will feel it." Fox Gabriel turned around and Kevin could've sworn he glared.

Kevin swallowed hard and Team Free Will, after a few moments, broke through the entrance to the Fourth Realm.

-8-8-8-8-8-8-

Dean felt slightly awkward walking in front of Castiel right now while he was in the form of a hawk, but as a man who'd grown up in the life of weird it also wasn't that freaky. Even so it still was a tiny bit unnerving having a six foot bird staring down his back.

"I can shrink my form," hawk Castiel said. "If my size makes you uncomfortable."

"That entire sentence had perverted undertones." Dean replied.

"I apologize." hawk Castiel chirped once and a mist engulfed him before he shrunk down to the size of a regular hawk. He flew up and landed on Dean's shoulder. He preened a few of his feathers and cocked his head in typical Castiel fashion. Dean chuckled and petted his head.

"Never change Cas." Dean said.

As they approached Demontown the stench got worse. Many decaying, crumbling, blackened ivy covered buildings suddenly surrounded them. Numerous pairs of glowing eyes watched from windows, doors, and various alleyways between buildings with absent bodies shrouded in darkness. It was like the Croatoan virus infected future Dean had been sent to with orgy loving drugged up Castiel and Lucifer indeed wearing his brother to the prom. Kevin gulped. Dean rubbed his palm with his fingers, Sam tensed up a bit, Castiel, Titan, Gabriel, and Crowley walked along calmly and without a word. They strode forward stoically step by step as if they'd traveled these roads a million times before and Dean suspected that Crowley had. His stomached turned when he heard an audible hissing sound coming from behind them. They turned around just in time to see a dark haired figure launching itself at them. It landed right on top of Sam and growled. Sam glared.

"Ruby..." Sam grumbled and struggled to get free and reach the knife that she'd stupidly given him many years ago.

"Surprise Sammy boy," Ruby smirked. She was covered in blood and her eyes radiated evil. "Have you finally come to join your brethren?"

"No way in Hell!" Sam yelled as she got off of him and they stood facing one another, both poised and ready to attack the other.

"Well ya see Sam that's kind of a contradiction right now isn't it?" she smirked and let out a menacing laugh. Sam reached for the knife, but it was not on him. He let out a tiny gasp. "This boyfriend of yours, Gabriel? He's pretty. Too bad you'll never get another chance to tell him that."

Ruby lunged and Sam shielded his face with his hands. He heard a shriek and he was faced with Ruby's once again dead eyes. Dean was right behind her with the knife in her back. He unsheathed it from her skin and she fell in a heap lifeless to the ground. The other demons around them hissed and yowled.

"We should get moving like yesterday," Crowley exclaimed. "You killed one of their own and now they're pissed!"

"In other words…" Kevin swallowed hard.

"Run, again!" Dean exclaimed and everyone took off in front of them. Dean tried to stay close to the others, but he found himself separated. Not even Titan was by his side. He did have Ruby's knife though, that was a small perk in the situation he'd found himself in. He kept moving forward as he ran hard. His legs ached eventually, but demon after demon was on his tail. They were jumping down from buildings, out of windows, knocked over trash cans in alleyways and high-tailed it after Dean. He was easy prey right now, out in the open and seemingly defenseless. Dean tripped once on a rock and that alone slowed him down. He could feel his knees giving out and his heart beating faster and faster. He clutched his chest, but kept going. Suddenly though, he felt a hand grab his jacket collar and pull him quickly into a building before the demons even knew what hit them. They just kept running. Dean tried to see who'd grabbed him, but in the darkness he couldn't. It wasn't until he saw those eyes, the glowing eyes. He assumed he was toast.

"Well Clarence failed to mention you were here too?" a familiar voice said and a female figure stepped out of the shadows.

"Meg?" Dean said, breathlessly. "What the hell?"

"Your friends are in the back. They got here first." Meg helped Dean up and motioned for him to follow her. "C'mon Dean."

**Notes for the Chapter:**

> Reviews are appreciated!


	8. Meg

**Summary for the Chapter:**

> Meg provides Team Free Will with a place to stay for the night and she and Titan have a heart to heart talk.

The back room of the abandoned building was seemingly warmer than the surrounding air. Dean soon realized Meg had a fire going in the living room fireplace. Considering where they were and how stupid the rest of the demons had been earlier, Dean figured that it didn't give her away at all. There were two old couches surrounding the fire and there sat all of Team Free Will and Jimmy. Titan barked excitedly and ran up to Dean.

"Woah easy there boy," Dean laughed. "I'm okay."

Titan barked and ran back towards the fire. He curled up in front of it and sighed contently.

"He was going crazy," Crowley informed a tired and ragged Dean. "And so was Castiel. Neither one of them would shut up."

"I'm fine, Cas." Dean smiled and waved to the angel. He walked closer to Castiel and sat down next to him. Meg stared at them, the happy, relieved smiling, the gestures, and then when Dean kissed Castiel on the cheek Meg felt a surge of red hot jealously sweep over her. She sighed hard and turned away to tend to the flames. Sam kissed Gabriel warmly, the pair was sitting closest to the fire as it crackled and danced in the hearth. Jimmy sat next to Kevin; both held much needed glasses of water in their hands. Meg thrust one into Dean's hand a little forcefully; he thanked her none the less.

"You guys can stay here tonight," she said. "I'll help you to the Fifth Realm, but after that I gotta stay here."

Crowley nodded. Everyone else was too caught up in the warmth and nourishment to comment. Gabriel snuggled close to Sam and proceeded to kiss his chin and play with his long hair. Sam chuckled, but kept his eyes focused on the flames. Jimmy settled back into the pillows on the couch and sighed, closing his eyes. Kevin looked over at him for a moment before pulling out his phone. He remarkably found that he indeed, did have service. He pulled out the piece of paper in his pocket and entered the number into his contacts. He didn't know why, but he sent a quick text to Ron.

'Hey Ron its Kevin. We're almost there thank god. We're in the Fourth Realm already. Thanks for getting us where you did.'

Kevin waited a few minutes and then he indeed got a reply.

No problemo Kev. Anything for someone cool like you and his friends. Truth is ya'll are probably the most interesting passengers I've ever had. You need anything, you call me. Ya dig? Stay safe K-dog.

Kevin smiled at the newly appointed nickname and put his phone back in his pocket before closing his eyes to fall asleep.

-8-8-8-8-8-8-

Meg had managed to somehow provide sustenance as well as shelter. She came out with plates of food stacked high with sandwiches and chips. She passed each one out and even one to Titan, who gladly changed into his human to eat it. Dean tried not to think about the fact that Titan had practically almost slobbered all over his face earlier in relief. Gabriel and Castiel had both ceased to be in their spirit guide forms which in reality Dean found highly interesting. He'd seen hawks loads of times on all of his excursions, now he could only wonder if one of them had been Castiel, watching him from afar at all times.

"A lot of times it was me," Castiel spoke up to the hunter. "Sometimes though, it was actually just a normal hawk."

Dean forgot the angel could read minds and he nodded in response.

"Good to know." Dean took a bite of his delicious sandwich and set the plate down. "Do you have any idea what the next Realm could be?"

"I only by-passed the first two to get to your soul Dean," Castiel replied. "I didn't even know the others existed until now, so no, I haven't the slightest idea."

"I'd ask our demon friend over there," Dean smiled and motioned towards Crowley who currently had his eyes closed. "But he's down and out."

"Well whatever it is," Castiel nodded with reassurance and took Dean's hand in his. "We'll take it on like we always do; I do believe the saying is 'guns blazing'?"

"Now you're learning," Dean chuckled and placed a small kiss on Castiel's lips. "When we get back to the bunker I am teaching you about classic films."

"I think I'd like that." Castiel smiled.

Meg rolled her eyes from across the room, but it went unnoticed by both Dean and Castiel. The whole scene sickened her, even though she knew it shouldn't. Things had changed since she walked the earth and then died (it was hard enough having Castiel in the same house as her, much less Crowley, her killer). Lots of things had changed. She had tried to convince herself time and time again of the facts, but that didn't mean it hurt any less. She collected Jimmy's and Kevin's dishes and walked towards the kitchen.

"I'm headed out for a little bit," she informed them all. "I'll be back soon, I'm going to see where those buffoons went and see if I can't get them off your trail before morning."

She placed the dishes in the sink and grabbed her jacket from the peg on the wall. She grabbed a knife from the drawer in the old rickety desk that sat by the crumbling and ruined staircase and stepped out the back door to the outside world, shutting it quietly behind her.

-8-8-8-8-8-8-

Meg walked down the streets quietly and stealthily. She used darkness as her friend and stayed within its reach on the corners of streets and alleyways. There was no sign of demons anywhere, it was almost eerie, but Meg figured they were all long gone by now, searching the deeper depths of Demontown for their human prey.

Meg didn't like Abbadon at all. Crowley hadn't been much of a prize either, but at least he hadn't been hell-bent on enslaving his own kind and using them for his dirty work. They'd all had their own minds, even when he'd become King of Hell. Meg gripped the blade of the knife tight enough so that a small trickle of blood fell from her thumb, but not enough to cut it fully. She'd only wanted to feel something. She'd needed to get away from the house.

"That's no way to handle it that's for sure."

She turned to see Titan in his Angelhound form, and she cursed under her breath. He'd obviously been following her a ways away from the safe house and had finally decided to show himself. Titan's eyes flashed white before he shifted into his human form and he started walking closer towards her.

"Oh cram it," Meg glared, but she couldn't bring herself to be mad at him. "What would you know about it all, you're just a damn dog!"

"It may be true that I am just a dog in most people's eyes," Titan chuckled and sat down next to her, his bleach blonde hair falling to the sides of his face. Meg tried not to cry, especially not in front of him. No doubt he'd run back to Dean with everything she'd tell him and gossip. The only Heavenly entity she'd ever trusted was Castiel and he had stabbed her in the back too. "But, that doesn't mean I'm not human as well."

"So you can do a few tricks," Meg wiped her eyes and sniffled a bit, it was no use she'd broken down and started crying in front of Titan. "It doesn't mean you'd even begin to understand how I feel."

"Why don't you try me," Titan said, facing her and waiting for her to speak. "I might understand more than you think."

"I guess all roads lead to love right now." Meg said.

"Isn't that always the problem right there," Titan replied. "Love is the root of all evil, screw money."

Meg laughed and wiped her other eye.

"Anyway," Meg continued. "I guess you noticed my silent objection to Dean and Clarence's PDA. It's just not fair, but I guess nothing is."

"Now see that is where doubting me is wrong," Titan chuckled and pointed a finger at her. "Because I do know how that feels."

"Jealousy?" Meg asked and Titan nodded.

"Angelhounds have the same quota in Heaven as angels are supposed to uphold," Titan explained. "No love, no showing of emotions, no thoughts of our own. But every once in awhile you meet that one girl or boy I mean if one of us swings that way which would be very hard to tell since we're all part hound. Anyway I'm rambling; I was supposed to watch over this one woman once an enormously long time ago. Now try falling for a person and you're not even allowed to change forms, not allowed to be human once. Your only job is to protect and serve her. Needless to say she ended up marrying this douche, well in my eyes he was since he got to her first, he was actually a wonderful man, I ran off one day later and I was sent back to Heaven as my job was done. I never saw her again."

"Yeah well try being kissed by an angel thinking he's in love with you," Meg shot back. "But in reality he's pining after some stupid human who has a death wish. Someone he can't even have forever because eventually that human will die and he'll be all alone, wandering for his 'lost love' or some bullshit like that and he'll never even give a second thought to the girl whose been waiting in the background and running after him for years. He was supposed to by my unicorn not Dean's..."

"I had reason to believe you were talking about Castiel," Titan sighed. "We can't help who we fall in love with, I suppose."

Meg tossed a rock at the brick wall of the alley and sighed. Titan leaned his head into the wall, looking up at the black sky. Luckily the garbage in the dumpster nearby wasn't filled so it didn't smell at all.

"We can try." Meg sighed again and crossed her arms.

"Castiel is very much in love with Dean," Titan informed her. "And Dean is very much in love with Castiel."

"Thank you dickbag," Meg grumbled. "For reminding me of that little fact."

"But," Titan interrupted her. "That doesn't mean that you or anyone else has a right to interfere."

"I know…" Meg found herself sighing harder this time. "Believe me I know. I do want Clarence to be happy. Dean too I suppose. I just feel cheated, like I'd finally found the one ya know? Then the universe decides that it's gonna try and be funny and take him away from me."

"I can inform you with the utmost confidence," Titan said. "That you will indeed find 'the one' one day as I have witnessed for thousands of years with millions of individuals."

"You better not be pulling my leg hound," Meg laughed. "Or humping it."

"Oh so now its dog jokes," Titan laughed. "Gee thanks there's nothing I can't stand more."

"Anytime," Meg stood up and helped him up as well. His hand felt soft and Meg tried not to think of it as being a paw half of the time. "Hey listen don't tell anyone I'm being soft…but thank you."

"Anytime." Titan smiled at her. His eyes shone white once before he turned and ran off in his Angelhound form down to the end of the alleyway. He looked back and Meg smirked, trying to hide the fluttering of her heart in her chest. It had been so long since someone had been so nice to her, how could she help it? Titan then tore off back towards the house down the streets of Demontown.

-8-8-8-8-8-8-

The fire had died sometime in the wee morning hours when Dean awoke. He looked over at Castiel, who was sleeping soundly next to him and smiled. He forgot for a mere moment about where they were and what they were working their way towards. When those thoughts entered his mind, his smile fell and he sighed. He ruffled Castiel's hair, something he enjoyed doing when the angel was sleeping next to him in the bunker.

The bunker. Dean had spoken to Castiel briefly about their lives after all of this. First things first he and Castiel were going to have sex, no questions asked. It was something Castiel wanted and Dean was more than willing to oblige. It would be new to him too after all, but he knew that it would work out in the end. Dean hadn't really pictured his future in any way. He'd always assumed he'd die before anything significant would happen to him. Now, here he was, staring his future in the face and he was honestly a little scared. Castiel meant so much to him, more than others before had. He didn't want one thing to go wrong, but he also was a realist and he knew there would be mishaps. That came along with the territory of being a Winchester.

He looked over at Gabriel who had just begun to try and wake up Sam. He hadn't really talked to Sam either about his plans with Gabriel. Both he and Castiel had obligations towards Heaven. They were angels after all, at least after this they wouldn't have to worry about demons and other hellish creatures that crawled up from Hell's depths.

Dean heard the door creak and Meg walked back in, she'd been gone all night but Dean hadn't really noticed. It was hard to keep track of time in this Realm. Titan snuck through the door behind her on all fours and slunk over to Dean. Dean petted his head and his eyes shone white for a second in appreciation of the attention.

"Missed ya too buddy." Dean chuckled.

"I have an assortment of random food here and there for breakfast," Meg informed everyone who had awoken already and the others slowly did too. "After that I can take you to the Fifth Realm."

Castiel opened his eyes and Dean helped him up. Sporting a serious bed head, the angel smiled and kissed Dean's cheek. Dean smiled back and walked into the kitchen to get them some food. Meg's glare faded and she sighed again, but this time it was more a sigh of acceptance. She looked over at Titan who was looking back at her and she could've sworn she saw him smirk.

"Oh shut up," Meg laughed. "And stop looking at me like that!"

"Like what?" Titan spoke through her mind.

"Like a fresh piece of steak," Meg replied. "And that you told me so."

"Well I did tell you so," Titan replied and whined. "Also what did I say about the dog jokes? And unless you happen to have a huge hunk of steak in that somehow working fridge of yours don't even mention it."

-8-8-8-8-8-8-

Team Free Will set out early and they cautiously walked the streets. Meg and Crowley led the way with everyone else armed in the middle and Titan trailing the pack and protecting them from behind. The occasional noise made them jump but eventually they reached the end of the endless streets and there it was the portal to the Fifth Realm.

"As promised." Meg motioned to the glowing portal.

Gabriel and Sam went first and they disappeared with Crowley in tow right behind them. Kevin walked through without a word, but a small smile on his face that Dean wondered about. Dean took Castiel's hand and led him forward.

"Thanks Meg." Dean nodded and she smiled.

"Take care of Clarence," Meg nodded towards Castiel. "He's a troublemaker."

Castiel smiled a little.

"Damn if he isn't." Dean chuckled and he and Castiel stepped through the portal.

"Good job there princess," Titan barked and looked up at her. "I knew ya had it in you."

"Oh shush," Meg felt her cheeks flush ever so slightly. "Go save the world or something."

"Way ahead of ya." Titan's eyes flashed white and he too jumped through the portal to the awaiting other side.

**Notes for the Chapter:**

> Reviews are appreciated!


	9. Hades

**Summary for the Chapter:**

> Team Free Will makes their way into the Fifth Realm of Hell: Hades' Domain. The God informs them of Abbadon's plans and provides them with a resting place for awhile.

The air in the Fifth Realm was almost too much to bear. Dean covered his eyes initially because it stung so badly. He coughed as the sulfur-like air around them surrounded their bodies and almost engulfed them. Castiel hacked a little as the smoke entered his lungs, but he, Titan, and Gabriel all seemed to have a higher tolerance. Crowley was basically immune. There was a terrible noise, a screeching and yowling sound. Dean tried desperately to uncover his stinging eyes and look around for the source, but every time he removed his arm the sulfuric air hit him like a brick to the face.

"Try to crawl forward!" Crowley yelled over the blasts of air. "It should die down once the portal closes!"

Dean nodded and kept a tight hold on Castiel's hand. Titan crawled nearby him, his fur shimmering in the wind as he let out a few whines. Gabriel had a hold on Sam as the pair climbed forward away from the tunnel-like portal. Kevin coughed, but he relentlessly crawled forward as well. Jimmy hadn't made a sound as he crawled alongside them. The portal shut closed with a snap and just like that the air was bearable once again. Dean sucked in a breath to test it and once he noticed it no longer burned his throat and chest, he opened his bleary eyes. They were at the foot of a rather large temple. Dean studied the intricate, ornate designs and decorations all over it. It was made entirely of well polished gray marble. It certainly looked expensive.

"Prime real estate in Hell," Dean joked as he pushed himself to his feet. "Who would've known? Sold!"

"I've seen these markings before…" Castiel trailed off and touched one of the pillars with his fingers. He seemed deep in thought, but unable to recall the memory from so long ago. He'd fought against something bearing similar marks, that was all he knew. Crowley huffed and dusted off his clothes before standing. Everyone else got to their feet one by one. Titan shook his head and whined, pawing his ears to rid them of the soot and sulfur. He sneezed once and then barked.

"I don't know Titan," Dean said. "I have no freakin idea where we are."

"Well then you obviously aren't the most cultured of humans…" an unfamiliar, but deep, voice said from the front of the temple's doors. Dean looked up, almost ready to unsheathe his knife. The man that stood there was a lanky man with dark hair and brown eyes which had an almost orange glow around them. He looked about thirty years old and he was deathly pale, but not in the sickly way. He wore a tight black t-shirt with skull and crossbones on it. He had tight dark blue skinny jeans to match and black shiny Doc Martens on his feet. He donned various jewelry pieces between both of his hands. He had three rings, one was a skull with deep red ruby eyes, the other a silver one with an Onyx in the center, and the third just another silver band with no distinct features where a wedding band would be placed. He looked over at the travelers in disdain and narrowed his eyes when he saw Crowley especially.

"Scuse me?" Sam asked, a bit put off by that comment.

"Forgive me, my people skills are rusty," the man strolled down the marble steps and stopped in front of the group. "I don't get visitors all that often. Hello Crowley."

"Hello Hades." Crowley said.

"Wait a second," Kevin exclaimed. "Hades?! Like the Greek God?!"

"You have your God," Hades replied. "And my people have their Gods. I just happen to be the one to guard their dead."

The group was still in disbelief of the man in front of them. They had heard of other deities, but had yet to come into contact with any with Greek or Roman ties until now. Castiel studied the marks again before staring at Hades. The God stared back at him.

"They told us about you," Castiel said. "They told us about you and your two brothers up in Heaven."

"That was a long time ago," Hades said and gave a little flick of his wrist, the torches leading up to the temple all lit at once. "You all had best take shelter in here for now. Abbadon has eyes and ears everywhere you know?"

The group hesitated a moment, wondering what Hades knew about Abbadon, but they figured they had no choice, but to take up his offer and so they followed him into the home, the doors shutting hard behind them.

-8-8-8-8-8-8-

The inside of the home was even more breathtaking than the outside. Its ceilings were high and despite the dark corners being overrun with tiny cobwebs, the place was clean. It was covered head to toe by marble floors and walls and fine stained glass donned the windows. To one side of the room was a table covered with an elaborate feast of various foods that looked good enough to eat. A golden throne like chair sat against the wall at the front of the room. Hades walked over to the table and mojoed up some wine out of smoke. He poured it into a wine glass and took a sip as his guests filed through the doors and they shut behind them.

"I heard pray tell that you all were headed this way," Hades said before taking a seat in the throne-chair. "And you Castiel, you've been the talk of the town down here for years. Ever since you rescued the Righteous Man from turning into barbecue."

"Um," Castiel didn't know how to respond. "Thank you I suppose…"

Dean suddenly heard a low growl and he spun his head around to see Titan, his rear end being violated by the big black muzzle of another dog.

"This is so degrading…" Titan whined and then spun around, growling at the all black dog that had assaulted his backside with its sniffer. The slightly bigger black dog with red eyes backed away ever so slightly.

"Cerberus is harmless," Hades commented. "Unless of course you piss me off. Then he does whatever daddy tells him to."

Titan growled once more and flicked his tail in Cerberus' face causing the other dog to sniffle and whine once more. Dean laughed as he eyed the tantalizing food on the long table. Sam and Kevin both had been studying the ancient paintings and manuscripts framed and hung on the walls.

"It is quite amazing you know," Hades walked over towards the younger Winchester and pointing to a particular manuscript. "How far you humans have come since my time in that world."

"Even after all the horrible and annoying things we've done you still are fascinated by us?" Sam asked.

"Yes," Hades replied. "Even after all that. It is not as though I have not made mistakes of my own to rival yours."

Dean grabbed a plate of food and was about to take a bite when he felt pressure against his legs. He looked down to see Titan pressed in between his legs.

"What is it Titan," Dean asked with a small laugh. "Cat got your tongue?"

"Very funny wise guy," Titan whined. "No, this soot covered mutt won't leave my behind alone!"

Dean's eyes went to Cerberus' who seemed confused and hurt that Titan had run away.

"I think he likes you." Dean whispered.

"Oh Heaven no," Titan stepped out and faced him, his eyes shone white. "You ever heard of personal space buddy? Well my ass is off limits!"

Titan motioned to his whole body with his head. Cerberus still seemed confused, a little drool dripping from his muzzle and onto the floor. Suddenly a small ray of light shot out and Titan changed into his human form.

"No touchy compadre," Titan huffed and motioned to his whole body with his hands. "I don't swing that way!"

Cerberus now seemed scared and backed away a little. Titan changed back into his Angelhound form and huffed.

"Good riddance." He said.

Hades chuckled and drank the rest of his wine. Castiel stared silently off into space and Crowley remained silent as well. Dean could tell Crowley was anxious, he just wanted this all to be over. This hurry up and wait was not comforting to him in any way. Dean walked over closer to him.

"Good eats huh?" he commented, putting another roll on his plate.

"Yes Hades did always know how to throw a party," Crowley replied. "And put on a show."

"Are you nervous?" Dean asked he didn't even have to mention why.

"Nervous? I don't get nervous," Crowley replied, looking around at the others. "Anxious and impatient though, I do become that after awhile."

"Look none of them have ever been this deep before," Dean said, referring to Hell and motioning to his friends and family. "Not even me. We're all a little spooked. I mean there's a chance none of us will make it out of this alive."

"I know," Crowley sighed and looked over at everyone conversing again, they were laughing a little sure, but there was this hint of fear in all of their eyes. "Dean if I tell you something, will you tell no one else?"

"Sure Crowley." This sure sounded familiar, hadn't those words come out of Castiel's mouth so many years ago?

"I never intended to make it this far," Crowley lowered his voice to a whisper. "There's a price on my head, squirrel. A very high price at that. I never intended to drag you all into this mess. I was actually going to take out Abbadon alone."

"She would've killed you." Dean said.

"That's the point," Crowley said. "This is my war; she has convinced every demon that I'm the next target. I'm a walking blimp on her map just being down here with all of you. I guess what I'm trying to say is, when the time comes I want all of you to go for the exit and don't worry about me."

"Damn it Crowley," Dean cursed under his breath and glared at the ex-demon. "Look you may be the biggest pain in the ass to ever exist, but you are not going in guns blazing suicidal you hear me? Whether you like it or not we're all in this together. And whether you like it or not this affects all of us and all of humanity as well. This isn't just your war anymore. You called me for help and that's what I intend to bring with me and I did. So, whatever happens in that next Realm we're all going to make it through this one way or another alive!"

"You don't give yourself enough credit Winchester," Crowley chuckled a small smile broke through. "You got me all tingly inside with that speech."

"It's kind of my job to motivate people to kill things in case you hadn't noticed." Dean said. "So do we have a deal? And no kissing this time."

"No kissing," Crowley replied. "And yes, we have a deal."

"Good." Dean nodded.

-8-8-8-8-8-8-

A few glasses clinked here and there, but much conversation ensued. Hades, it turns out was also quite the storyteller. He had a wealth of information and ancient tales to tell and the group listened intently as he regaled each one. Castiel and Gabriel listened intently, remembering what they'd learned from the Scholars up in Heaven about Hades and his two brothers. Castiel didn't judge the God for what he'd done, but he noted the fact that Hades neglected to share all of the details with everyone. Eventually the doors nearby opened and Ron appeared in them, claiming his shift was over and it was time for his 'old man' to take charge. Dean watched Kevin's face light up when the boat pusher entered the room and hugged everyone, Kevin felt Ron giving him a pat on the back and remarked on how alive he looked in the place considering how dark it was. Ron chuckled in response to the Prophet and made his way over towards Hades. The God hugged him like he held him in the highest regard and Dean could've sworn he saw the God smile. The rest of the feasting went along as it had before, but with talk of something other than Abbadon from the two young boys.

"Okay well I got to level three hundred and five!" Kevin argued and Ron scoffed.

"Okay well I'm on level five hundred, beat that." Ron smirked.

"Dude that one boss is impossible with a capital I," Kevin whined. "How in the hell did you get past it?"

"It gets boring down here sometimes, okay scratch that like all the time," Ron replied. "And one day when I'm not pushing a giant hunk of wood down the Styx I'll show you exactly how I did it."

"That sounds great." Kevin replied.

Suddenly the giant clock on the wall chimed eerily and loudly throughout the whole home. Hades looked up at it and sighed heavily. He stood from the table and started rummaging through the drawers on the dresser near the door.

"What is it?" Sam asked.

"That bitch Abbadon," Hades said, pulling out a small brown bag that looked as if it was glowing. "She's been rallying her forces, attempting a final takeover of Hell and earth which she claimed would happen on the fifth Sunday of this year. Four hours ago it was Saturday. You all don't have much time if you want any hope of seeing her in person."

"Great." Dean muttered.

"These," Hades opened the bag and several blue, glowing orbs rolled out onto the table. "Will help get you out of here once you reach the epicenter of Hell. I have no control over what happens in the middle at least not right now. Persephone used these for travel to Olympus and anywhere else she needed to go in her time down here with me. Throw them on the ground, a beam of light will come up and you have to visualize in your head where you'd like to go and they'll take you there."

"Sweet." Kevin exclaimed and grabbed one, pocketing it.

"Sounds like a plan." Sam said and grabbed one as well.

Everyone picked one off of the table and put it in their pockets. Dean fiddled with his a little, knowing it was close. They were going to see Abbadon and they were going to have a chance to beat her.

"I have enough power to transport you into the Sixth Realm," Hades said, tossing the bag aside. "But I have no control of what happens to you once you get there."

Dean and the others gathered at the center of the room where Hades had conjured up a portal to the next Realm. Everyone was filled with an overwhelming feeling of dread.

"Wait!" Ron called out and stood with them. "I'm going too!"

"Ron..." Hades tried to protest, but Ron wouldn't hear him.

"Ron," Kevin said. "You're gonna get yourself killed. Have you met Abbadon?"

"Rule number one," Ron patted Kevin on the shoulder. "A bro never leaves another bro during his death match. And yes I've met the bitch. I'd like to sucker punch her myself too. Where else am I going to get that opportunity?"

"Gee thanks you make it seem so…deadly." Kevin gulped.

"Do not fret K-dog," Ron winked at him. "I've got your six."

"We can do this Sammy." Gabriel reassured the hunter and Sam nodded.

Titan stood stoically and stared up at Crowley with a reassuring look. Crowley returned the gaze. They both were seasoned warriors falling into line for battle.

Dean looked at Castiel. Castiel looked at Dean. The pair locked hands tightly and Castiel's gate went from doting sidekick to Warrior angel in two point five seconds. He smiled at Dean.

"We've done scarier things before Cas," Dean said. "We've got this."

"That we do Dean." Castiel nodded and looked forward.

With that, Hades flicked his wrist and they were gone in a cloud of smoke and ash. The group vanished before his very eyes and he let out a deep sigh.

"Oh this will be a bloody Sunday indeed." he said to himself.

**Notes for the Chapter:**

> Reviews are appreciated!


	10. Abbadon

**Summary for the Chapter:**

> Team Free Will and company meets Abbadon head on for the battle to close Hell before she opens it to the earth.

His chest was hot, but the air around him was freezing and Dean took in a shaky breath that almost stung. It was lighter than he'd expected it to be in the epicenter of Hell. Dean had let go of Castiel's hand when they'd arrived and he'd immediately reached for his knife. He didn't know why exactly. It wouldn't help him against a Hell Knight. But it was instinct from all of his years as a hunter.

"If she's really in here," Crowley said quietly. "She'll make her presence known."

"Maybe not," Jimmy chimed in and everyone held their breath. "Maybe that's just what she wants you to think."

"Jimmy's right," Gabriel remarked. "Just keep your eyes open, ain't no rest for the wicked here."

Gabriel was right. This wasn't Heaven, this was ruthless Hell and there were no rules to protect Team Free Will now. They were Abbadon's precious human bait and Dean knew deep in his gut she'd show no mercy. The seconds ticked on slowly, agonizingly slowly, but yet no one emerged from the shadows. It was as if she was playing a game with them, keeping them on edge just long enough so that she could strike out of nowhere and dig her talons into their flesh and being. Dean's senses were heightened. He could hear every drop of every piece of rock that shifted, every hiss and scurry from every hidden demon, and every breath he took. His heart pounded in his chest the same way it did before any fight.

"It's cool K-dog," Ron stood protectively in front of Kevin, who was shaking something awful and not meaning to. Ron put his hand on Kevin's arm to calm him. The boat pusher materialized a knife with strange markings in his hand and Kevin couldn't help, but stare. "I've got you."

"H-How did you do that?" Kevin asked quietly.

"It's a Hellboy staple," Ron explained as he looked all around for Abbadon. "We all know how to do this."

"We? As in there's more than one of you?" Kevin was so confused.

"I'll explain when we're not in a 'do or die' situation Kev." Ron replied and Kevin could've sworn he'd seen the boy's eyes go red for a split second. He played it off as a trick of the light though.

Titan growled low in his throat as he stood by Dean, hackles up and ready to fight. Dean stood close by him; he'd found he could rely on the Angelhound to kick ass and take names if need be. Sam and Gabriel stood side by side; together they made a fierce team made up of pure strength and determination. Crowley stood without much cause for alarm; he didn't seem fazed by any of it. Jimmy stood beside his doppelganger, Castiel and tried hard to keep his heart from pounding out of his disembodied chest.

Dean whipped his head to the side; he'd heard a rather interesting arraignment of sounds. It almost sounded like footsteps. If it was Abbadon, they needed to get the jump on her, if it wasn't he'd be best suited to stay put, but something drew him to the corner. Knife raised, he carefully stepped towards the darkness and swung. The figure fought hard, but didn't quite resemble a Hell Knight.

"Jesus Winchester!" Meg exclaimed, barely missing his blow.

"Meg! What the hell!" he exclaimed, still trying to keep his voice low. "What are you doing here? More importantly how are you here?"

"Look," Meg sighed and came out of the shadows. "After you all left the Fourth Realm I knew that it would be basically suicide for all of you to just waltz right in here expecting the seven of you could beat a Knight of Hell so I did what no lower level demon has ever thought of doing before and I broke out of my Realm and somehow made it here without so much as a scratch. That is before you almost took my head off. I was trying to get here before you and maybe block her off, but you kinda screwed the pooch on that one."

Titan barked once, annoyed.

"No offense Titan." Meg said.

"Look Meg we appreciate the help," Dean bit his tongue nervously it felt foreign to say his half-brother's name. "But the least amount of lives we lose the better."

"Well since I managed to somehow get here," Meg crossed her arms and twirled a knife in one of her hands. "You can count me in."

Titan whined; quiet enough so no one heard him. He didn't want her fighting this fight. He could only protect so many people and technically speaking Dean was supposed to be his priority. Why did he even feel forced to choose? He hadn't felt protective over a demon, well ever. It was his job to kill them and to never look back. Why was he feeling so protective over someone he'd just met?

"Well what do we have here…" a familiar ominous voice said from the shadows and Titan growled loudly. Dean spun around only to be greeted by Abbadon, emerging from the protection of the shadows, unarmed, but Dean knew she had an ace up her sleeve regardless. The others made a formation beside Dean, weapons or hands raised, ready to attack.

"Hey bitch." Dean twirled his knife. "Miss me?"

"Dean Winchester," Abbadon chuckled and walked over to him, she circled him once tracing his chin with her fingernails and tickling it slightly. Dean swallowed hard and Castiel's eyes shone with jealousy. "I didn't expect for you to make it this far. I must say, I'm impressed."

"Where's my medal?" Dean grunted and shifted uncomfortably as her eyes watched his every move.

"It's at the cleaners." Abbadon joked back and walked away from him a little ways.

"Figures," Dean replied sarcastically. "And I was so looking forward to that."

"Cut to the chase Abbadon," Sam spat. "You have us, we're what you want, so come and get us!"

"Silly demon boy," Abbadon cackled. "Now you know I can't exhaust myself running after such handsome things as you all can I? No, I fear I've got a much bloodier agenda."

"Don't worry guys," Dean tried to egg her on. "She's a coward. She's just too afraid to fight us herself."

"Me? A coward?" Abbadon pointed to her chest and laughed loudly. "I'm afraid you are gravely mistaken Dean Winchester, if anyone is a coward it's these worthless idiots Crowley liked to call demons!"

"And just what exactly are you implying?" Castiel stalled her, trying to determine their best plan of attack.

"These fools are weak!" Abbadon yelled. "They don't even know what orders are anymore! They're not warriors! They are just lie down and bare their throats like puppy dogs to anyone who comes near! This one especially."

She pointed towards Meg and suddenly Meg felt herself being lifted and flung through the air. Next thing she knew she was dangling from the nearby cliff, her fingers barely able to hold on. Titan, who normally would never have broken his stoic nature, did so to his own surprise. He ran over to where she was hanging, noticing the innate fear suddenly in her eyes. She stared up at him and he moved without thinking.

"Meg!" He exclaimed, panting from adrenaline. He grabbed her jacket with his fangs and held on tight. His grip was unwavering and he dug his claws into the dirt beneath him to keep his footing. He held onto her tight, not thinking about the mess behind him.

"How cute," Abbadon giggled. "And now that Dean is without his prized protection…"

With that Abbadon struck Dean in the shoulder, knocking him to the ground and he groaned in pain. Low hisses that grew louder and louder came from the shadows and demon after demon crawled out. Abbadon let out a loud cackle as the hisses engulfed the room and her willing minions swarmed. Sam and Gabriel stood back to back, the hunter's knife raised high and Gabriel's eyes shining white with power as they each gave each other a nod before slashing at demon after demon that came at them. 

"C'mon, is this all you've got," Ron slashed at demons like a seasoned veteran. If Kevin didn't know any better he'd have thought Ron had been doing it all of his life and something deep inside of him knew he wasn't wrong. "You guys think you're so tough?! You've clearly never fought against a Hellboy before!"

Kevin let out a loud grunt and slashed at the air, killing a demon. He triumphantly yelled afterwards and with a quick gaze towards Ron the pair continued on fighting.

Titan pulled Meg up from where she was dangling, using all of his strength to do it. She collapsed nearby him, but quickly regained her momentum after she knew she was safe. She got to her feet and took off as she spotted a horde of demons making their way towards Sam and Gabriel. 

"Thanks mutt." she looked back only once.

"Don't mention it." Titan growled and went after more of Abbadon's minions emerging from the darkness.

Crowley eyed the Hell Knight. He studied her movements and waited for the perfect moment whilst he stabbed at his once loyal friends and minions. They all had looks of spite in their eyes while he felt their vessels' blood trickle down their backs with every stab. He gritted his teeth though and continued. Jimmy and Castiel made quite the pair as well, smiting and stabbing. They covered each other perfectly and mimicked each other's fighting styles. It probably came in handy that Jimmy had once housed Castiel.

Dean was left alone.

It wasn't foreign to him, he'd fought alone before without Sam by his side, but this time it felt different. It felt as if it was him against the world. Like he was a lonely brown mouse in a cage of cats. He twirled his knife, trying to grasp the right angle, but it didn't come to him this time.

"Dean, oh Dean," Abbadon closed in on him. "Don't you ever know when to give up?"

"Sorry sweet cheeks," Dean watched Titan, his supposed back up, as he desperately tried to keep back her advancing forces. "But it ain't in my vocabulary."

"I've noticed," Abbadon's fist collided with Dean's jaw and the hunter staggered backwards, blood dripping from his mouth. "The man who cheated Heaven, who cheated Fate, who cheated Hell even, who's cheated us all. The man who dared to alter the future and the Apocalypse at that. That was a beautiful disaster that you wrecked Dean Winchester. You truly are the Righteous Man in Heaven's eyes."

Dean felt another blow and then another. So many hits were coming at him, his vision begun to blur and his eyes watered with a mixture of tears and blood. He tasted iron, salt, and sulfur on his tongue and he gasped for air even though he had enough. His hands begun to shake as he lifted the knife, but Abbadon kicked his chest hard sending him falling to the ground on his side, staring up at her.

"Forget the Apocalypse Dean Winchester, you are the most beautiful disaster of them all," Abbadon smirked evilly and lifted her arm to strike. "Say your prayers, you'll need them."

Dean closed his eyes and prepared for the blow, but it never came.

He slowly opened his eyes, Abbadon gasped above him clutching her stomach. Crowley stood behind her, knife through her gut.

"You really love to hear yourself talk don't you, you bloody princess?" Crowley rolled his eyes and pulled the knife out. Abbadon fell to the ground in a heap, dead.

Crowley helped Dean to his feet and the pair watched Abbadon's body slowly disintegrate and wither away, leaving the foul stench of sulfur behind. 

Titan stood by the others, still guarding them though the threat had ceased and all of the demons had ran away back into the depths of Hell.

"I think you're good Colombo," Meg touched her hand to Titan's back and the hound spun around to look at her. "But...thank you for saving my life."

"What else was I supposed to do just let you fall?" Titan asked, cocking his head.

"Ah shut up." Meg felt heat in her cheeks, but ignored it. 

"Boss level defeated K-dog!" Ron smirked and hugged Kevin tight, earning one red faced Prophet. Dean laughed and stumbled over to Castiel. He and Jimmy were bruised a little, but otherwise fine.

"Cas." Dean said breathlessly as if he was saying it for the first time. He cupped Castiel's cheeks and kissed him hard. Castiel's breaths were ragged, but his heart was now racing. Sam and Gabriel embraced in a similar fashion. Jimmy smiled and Crowley found himself doing so too.

Suddenly though, all of the demons around them in the caverns started shrieking and withering away. Their cries were far from human and they sounded as though they were in immense pain...or danger. The cave where they all stood started to shake and the rocks were coming loose. Everyone jumped and reached for their weapons. Titan growled.

"She had it under some kind of binding spell," Crowley yelled over the rumbling. "If she died it died with her!"

"We have to get out of here before it collapses!" Gabriel yelled.

"The orbs!" Kevin yelled and grabbed his from his pocket, slamming it to the ground and a beam of light shot up. Everyone grabbed an orb from their pocket and slammed it against the ground until they found themselves faced with a problem.

"We don't have enough Dean!" Sam yelled. He and Gabriel each had one, Kevin as well. Jimmy did, and Castiel and Dean did as well as one for Titan. Hades hadn't warned them, but things never did turn out as planned.

"You all go!" Crowley yelled. "I'll stay!"

"Crowley we talked about this!" Dean exclaimed and the chasm shook harder.

"Look squirrel you have limited time," Crowley yelled over the noise. "If you all don't get out of here soon you'll be trapped down here forever! This is my home and I know it better than anybody! I'll find a way out, but you all have to go!"

Titan looked to Meg and then to Dean.

"I'll be fine," Meg nodded at him. "Go! Your appointed needs you!"

"I'll come back for you," Titan barked. "I promise! You don't deserve penance down here!"

"Your mother ship is departing!" Meg said as Titan ran towards the blue beam of light that was his.

"Go be awesome upstairs K-dog!" Ron exclaimed and pushed Kevin towards his light. "Remember what I said! I always fulfill a promise!"

"Ron no, you can't you'll...die!" Kevin exclaimed. He didn't know why he cared so much. He'd only just met the boy. 

Everyone ran to their appointed beams. Dean took in a sharp breath and looked over at Castiel, whose eyes were closed. Castiel vanished first, followed by Gabriel, Jimmy, then Kevin, then Sam, and finally Titan. Dean took in one last breath, watching the three comrades that had helped them get to where they were now.

"See you on the other side Winchester!" Crowley saluted.

Dean closed his eyes and visualized the bunker right as the ceiling of the cave gave way and crashed to the floor below.

-8-8-8-8-8-8-

When Dean opened his eyes again he was no longer surrounded by sulfuric air and ashes. No dirt or fire remained. He was instead greeted by a familiar couch and coffee table. He rubbed his head and stood up slowly. They were in the bunker. They were home! Dean looked around for his friends and family, desperate to know if they'd made it home or not. 

"Cas!" he yelled and Castiel's head popped up.

Gabriel and Sam stood as well as Kevin and Titan shook his head, ridding himself of the grime of Hell. Gabriel and Sam embraced again, but more so in a hug this time. Sam held Gabriel tight and kissed him gently. Kevin let out cries to the man upstairs and yelled in triumph. Titan barked and ran over to Dean, making sure his charge was alright. Dean petted his head, but he was more focused on Castiel who was now making his way over to the hunter.

"Told you we could do it." Dean said as he pulled the angel close to him. His fingers running through Castiel's hair and the others playing with the buttons on his trench coat. His lips ghosted over Castiel's and a small smile broke out on his face.

"I had faith in us Dean," Castiel replied and kissed him. "Right from the start."

Dean laughed when he laid eyes on his family. All of whom were home, all of whom were safe, and all of whom were looking over at him.

"So?" he asked. "After all that who could go for a beer besides me?"

**Notes for the Chapter:**

> Reviews are appreciated!


	11. Epilogue

**Summary for the Chapter:**

> Team Free Will's journey into Hell is a success, but questions have still yet to be answered. Such as are their friends alive? And will there finally be peace for the Winchesters and their family?

**Notes for the Chapter:**

> It gets slightly smutty at the end of this, but nothing is said in great detail.

Team Free Will's excursion into Hell had been a success with maybe a few minor bumps in the road. Sam and Gabriel had decided to stay at the bunker, even though Dean had cut their romantic vacation short. They believed after all they had been through it was best to stick together. Dean sort of regretted that decision because as if late they'd been staring at one another with that look ever since they'd come back from the underworld. Kevin, who had previously been hard at work on the angel tablet, was finally able to take a break after so long and just relax. Dean had noticed a sort of emptiness about him though since they'd departed from down under. Dean never asked though, he let bygones be bygones. He knew they were all hurting from the loss of their friends and yet they were all trying to move on. Titan had been popping in and out of the bunker frequently due to his job in Heaven, or so he said. Dean didn't bother questioning him either. With the help of Gabriel and Castiel's powers combined, Jimmy had been able to get into Heaven safely and to the Sixth Realm for re-judgment. The Distinguished Angel Council had permitted his entrance into Heaven and that was where he was to remain for all eternity in the afterlife. Dean was happy for him.

As for Castiel, well Dean had promised him something special and that night he was determined to make do on his promise.

-8-8-8-8-8-

The bunker was quiet, not the eerie kind though, the good kind. It was the peaceful kind of quiet. Dean had dimmed the lights in his and Castiel's room and was currently pacing in the bathroom, trying to think of a good way to initiate this. It would be Castiel's first time doing anything of this sort and Dean wanted nothing more than to please him. The hunter rubbed his eyes and sighed.

"Screw it," he thought to himself. "I'll play it by ear, it's with Cas damn it. It'll be perfect either way."

Dean smiled at that thought and exited the bathroom, turning the light off behind him.

His smile only widened when he caught sight of the angel, sitting on the bed wearing nothing but his dark blue boxers and one of Dean's band t-shirts. Dean walked closer, sitting on the edge of the bed and smiling at Castiel. Castiel gave a small smile back, but then looked away quickly. His eyes darted to the sheets and he played with them in between his fingers.

"Are you nervous?" Dean broke the silence and climbed further onto the bed, sitting in front of his angel and letting his fingers run through Castiel's hair.

"Exceedingly." Castiel chuckled a little and finally made eye contact with the hunter, his smiling green eyed hunter.

"I have no expectations Cas." The bed creaked a little under Dean's weight as he gently pushed Castiel down into the sheets and climbed over top of him. He kissed his jaw and slowly, ever so slowly, started moving down towards his neck. His lips ghosted Castiel's ear and he whispered. "Just so you know."

"I-I know Dean…" Castiel shivered at the hunter's words and then met his eyes once more. Dean's eyes were filled with lust and were slightly hazy in the light. Castiel swallowed hard and Dean sensed his nervousness even more.

"I'll start," Dean said and pulled his shirt over his head, tossing it aside and onto the floor, he leaned in once again to whisper in Castiel's ear. "Don't you worry Cas? I'm gonna make you feel so good, better than Heaven ever could."

"D-Dean…" Castiel let out a tiny moan and watched as the hunter took the time to take down his pants slowly. Every one of his movements was carefully planned. Castiel's breathing hitched when Dean's fingers reached for the waistband on his boxers. The angel felt the hunter pull his boxers off, two fingers attached to the elastic, then move on to his t-shirt. Soon both were on the floor and Castiel was left naked underneath Dean. Dean's eyes looked over his torso and down to his legs. He had an almost hungry look in his eyes.

"You look so beautiful Cas," Dean's hands rubbed up against Castiel's hips. "You put Heaven to shame."

"D-Dean that feels…" Castiel moaned out, he was at a true loss for words.

"Sssh I know," Dean kissed his neck again, nipping at it. "I know it feels great doesn't it?"

Castiel touched Dean's abs, each muscle twitched with each movement of his fingers and soon the angel reached Dean's thigh. He caressed the inside of it and Dean groaned. Castiel's eyes moved over Dean's body, upon realization they were both naked Castiel blushed. He curled in a little, embarrassed to be completely exposed to anybody.

"You look incredible okay?" Dean cupped his cheek and smiled.

Castiel let out a shaky breath as Dean begun touching every inch of his body. Various noises exited the angel's mouth; Dean knew just where to touch. He knew what felt good and all in all so far Castiel was a groaning mess under the hunter's body. It seemed like hours before Dean finally had prepared him enough before slowly pushing into Castiel.

Castiel whimpered, at first with pain, but later with pleasure. Every move Dean made was like ecstasy. Castiel moaned, he groaned, his body covered in sweat as was Dean's. The sound of the hunter's breaths and moans in his ear was intoxicating. Castiel found he was almost drunk on it. Dean's hand gripped the back of Castiel's head as he crushed his lips against the angel's, every rock of his hips bringing them both closer and closer. He felt Castiel's fingers embed themselves into the muscles of his back. Dean groaned at the feeling.

Neither one of them could tell how much time had passed, neither one of them cared. They were both too caught up in the sweat and tangle of limbs that was each other. Castiel's eyes were glazed over with red hot lust and Dean found himself unable to hold back from ravishing the angel. Castiel's moans were erotic; they were like music to his ears. Passion and pleasure heightened as the minutes passed ever so slowly. Dean didn't know how to keep his hands to himself anymore. The rhythm they'd created was almost hypnotic and Dean doubted he could hold on much longer. Thankfully Castiel was first to push over the edge.

"D-Dean!" Castiel cried out, seeing stars in a white hot finish. He panted and cussed. At one point it was as if his orgasm had been in Enochian. Dean groaned and finished quickly after, pulling his angel close and panting, long, hot breaths on his neck. He stroked Castiel's hair as the angel came down from his high and his eyes met Dean's once again. The pair collapsed hard into the bed and Dean pulled the sheets over their sweaty, heated bodies. Dean, regardless of the heat, scooted over near Castiel and pulled him close. His hair tickled Dean's nose, but Dean didn't notice or care all that much. He was just savoring the way Castiel's body fit with his.

"Was that good?" he asked Castiel breathlessly as he ruffled the angel's hair.

"Yes Dean," Castiel nodded into Dean's chest. "I-It was…"

"I told you I'd keep my promise." Dean chuckled a little and moved the sticky little hairs from Castiel's forehead. The angel's blue eyes drooped. He was tired from their endeavor and Dean couldn't blame him. 

"Dean," Castiel closed his eyes and let out a deep breath. "Thank you."

"Anytime Cas," Dean kissed his forehead and with his free hand he clicked off the light next to the bed. "I love you."

"I love you too Dean." Castiel said. "Sleep well."

Castiel was fast asleep moments later, Dean shifted a bit so that he was facing his angel. He smiled.

"Sweet dreams," Dean whispered. "My angel."

**Notes for the Chapter:**

> Reviews are appreciated!

**Author's Note:**

> Reviews are appreciated!


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